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Journal articles on the topic 'Allylic alcohol'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 January 2023

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1

Ficeri, Vlastimír, Peter Kutschy, Milan Dzurilla, and Ján Imrich. "[3,3]- Versus [1,3]-Sigmatropic Rearrangement of O-Substituted Allyl N-Acylmonothiocarbamates." Collection of Czechoslovak Chemical Communications 59, no. 12 (1994): 2650–62. http://dx.doi.org/10.1135/cccc19942650.

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Substituted allylic alcohols (2-buten-1-ol, 1-buten-3-ol, cinnamyl alcohol and 3-methyl-2-buten-1-ol) react with acyl isothiocyanates (4-chlorobenzoyl, 2,6-difluorobenzoyl, 3-phenylpropenoyl, 2-thienocarbonyl, 3-chloro-2-thienocarbonyl and 3-chloro-2-benzo[b]thienocarbonyl isothiocyanate) with the formation of highly reactive O-substituted allyl N-acylmonothiocarbamates, which either spontaneously or by heating in boiling benzene undergo [3,3]-sigmatropic rearrangement to S-substituted allyl N-acylmonothiocarbamates. The structure of S-esters with isomerized allylic group affords the unequivoc

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2

Ying, Xiangxian, Yifang Wang, Bin Xiong та ін. "Characterization of an Allylic/Benzyl Alcohol Dehydrogenase from Yokenella sp. Strain WZY002, an Organism Potentially Useful for the Synthesis of α,β-Unsaturated Alcohols from Allylic Aldehydes and Ketones". Applied and Environmental Microbiology 80, № 8 (2014): 2399–409. http://dx.doi.org/10.1128/aem.03980-13.

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ABSTRACTA novel whole-cell biocatalyst with high allylic alcohol-oxidizing activities was screened and identified asYokenellasp. WZY002, which chemoselectively reduced the C=O bond of allylic aldehydes/ketones to the corresponding α,β-unsaturated alcohols at 30°C and pH 8.0. The strain also had the capacity of stereoselectively reducing aromatic ketones to (S)-enantioselective alcohols. The enzyme responsible for the predominant allylic/benzyl alcohol dehydrogenase activity was purified to homogeneity and designated YsADH (alcohol dehydrogenase fromYokenellasp.), which had a calculated subunit

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3

Jun, Chul-Ho, and Chang-Hee Lee. "Chelation-Assisted C–H and C–C Bond Activation of Allylic Alcohols by a Rh(I) Catalyst under Microwave Irradiation." Synlett 29, no. 06 (2017): 736–41. http://dx.doi.org/10.1055/s-0036-1591697.

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Chelation-assisted Rh(I)-catalyzed ketone synthesis from allylic alcohols and alkenes through C–H and C–C bond activations under microwave irradiation was developed. Aldimine is formed via olefin isomerization of allyl alcohol under Rh(I) catalysis and condensation with 2-amino-3-picoline, followed by continuous C–H and C–C bond activations to produce a dialkyl ketone. The addition of piperidine accelerates the reaction rate by promoting aldimine formation under microwave conditions.

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4

Li, Anding, Nan Zheng, Kai Guo, Zhongchao Zhang та Zhen Yang. "Electrocatalytic Isomerization of Allylic Alcohols: Straightforward Preparation of β-Aryl-Ketones". Catalysts 12, № 3 (2022): 333. http://dx.doi.org/10.3390/catal12030333.

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Electrochemical synthesis has been rapidly developing over the past few years. Here, we report a practical and eco-friendly electrocatalytic isomerization of allylic alcohols to their corresponding carbonyl compounds. This reaction can be carried out in undivided cells without the addition of external chemical oxidants and metal catalysts. Moreover, this reaction features a broad substrate scope including challenging allylic alcohols bearing tri- and tetra-substituted olefins and affords straightforward access to diverse β-aryl-ketones. Mechanistic investigations suggest that the reactions pro

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5

Liu, Qiaowen, Feng Han, Hongfeng Zhuang, Tong Zhang, Na Ji, and Chengxia Miao. "Direct deoxygenation of active allylic alcohols via metal-free catalysis." Organic & Biomolecular Chemistry 20, no. 8 (2022): 1680–89. http://dx.doi.org/10.1039/d1ob02168k.

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6

Ricigliano, J. W., та T. M. Penning. "Synthesis and evaluation of non-steroidal mechanism-based inactivators of 3α-hydroxysteroid dehydrogenase". Biochemical Journal 262, № 1 (1989): 139–49. http://dx.doi.org/10.1042/bj2620139.

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Two non-steroidal mechanism-based inactivators for 3 alpha-hydroxysteroid dehydrogenase (3 alpha-HSD) of rat liver have been synthesized: 1-(4′-nitrophenyl)-2-propen-1-ol (I), and 1-(4′-nitrophenyl)-2-propyn-1-ol (II). Both of these compounds inactivate homogeneous 3 alpha-HSD in a time- and concentration-dependent manner only in the presence of NAD+. Analysis of the pseudo-first-order inactivation data gave a Kd of 1.2 mM for the allylic alcohol and a t1/2 (time required to promote a 50% loss of enzyme activity) for the enzyme of less than 10 s at saturation. Similar inactivation studies with

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7

Kang, Ye-Won, and Hye-Young Jang. "NHC-catalyzed one-pot oxidation and oxidative esterification of allylic alcohols using TEMPO: the effect of alcohol additives." RSC Adv. 4, no. 84 (2014): 44486–90. http://dx.doi.org/10.1039/c4ra08133a.

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8

Wang, Jialiang, Wen Huang, Zhengxing Zhang, Xu Xiang, Ruiting Liu, and Xigeng Zhou. "FeCl3·6H2O Catalyzed Disproportionation of Allylic Alcohols and Selective Allylic Reduction of Allylic Alcohols and Their Derivatives with Benzyl Alcohol." Journal of Organic Chemistry 74, no. 9 (2009): 3299–304. http://dx.doi.org/10.1021/jo900070q.

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9

Abad, Alberto, Avelino Corma, and Hermenegildo García. "Supported gold nanoparticles for aerobic, solventless oxidation of allylic alcohols." Pure and Applied Chemistry 79, no. 11 (2007): 1847–54. http://dx.doi.org/10.1351/pac200779111847.

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After giving some general considerations about the specific properties of nanoparticles below 20 nm, procedures for size stabilization, and the importance of developing green alcohol oxidation reactions, catalytic data are presented showing that gold nanoparticles (3-7 nm) supported on nanoparticulated ceria (4 nm) are far more chemoselective than related palladium catalysts for the aerobic oxidation of allylic alcohols. Using palladium catalysts, in addition to minor oxidation of the alcohol functional group, we have also observed polymerization, 1-2 hydrogen shift, and hydrogenation. In cont

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10

Krainova, Gulnaz, Yulia Beloglazova, Maksim Dmitriev, and Victoria Grishko. "Stereoselective Epoxidation of Triterpenic Allylic Alcohols and Cytotoxicity Evaluation of Synthesized Compounds." Molecules 28, no. 2 (2023): 550. http://dx.doi.org/10.3390/molecules28020550.

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The epoxidation process of semi-synthetic triterpenoids 2-methyl-3-oxo-19β,28-epoxy- 18α-olean-1-ene, and its allylic alcohol derivatives were examined. 1,2α-epoxide, as the main product, was found to be formed from the starting enone exposed to m-chloroperbenzoic acid (mCPBA). In the case of hydroxy-directed mCPBA-oxidation of triterpenic allyl alcohols and their 3α-alkyl-substituted derivatives, inversion of C1 and C2 asymmetric centers with the formation of 1,2β-epoxyalcohols took place. The synthesis of 2,3α-epoxides was fulfilled from 2,3-dialkyl-substituted C(3) allyl alcohols by the act

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11

Akkarasamiyo, Sunisa, Somsak Ruchirawat, Poonsaksi Ploypradith та Joseph S. M. Samec. "Transition-Metal-Catalyzed Suzuki–Miyaura-Type Cross-Coupling Reactions of π-Activated Alcohols". Synthesis 52, № 05 (2020): 645–59. http://dx.doi.org/10.1055/s-0039-1690740.

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The Suzuki–Miyaura reaction is one of the most powerful tools for the formation of carbon–carbon bonds in organic synthesis. The utilization of alcohols in this powerful reaction is a challenging task. This short review covers progress in the transition-metal-catalyzed Suzuki–Miyaura-type cross-coupling reaction of π-activated alcohol, such as aryl, benzylic, allylic, propargylic and allenic alcohols, between 2000 and June 2019.1 Introduction2 Suzuki–Miyaura Cross-Coupling Reactions of Aryl Alcohols2.1 One-Pot Reactions with Pre-activation of the C–O Bond2.1.1 Palladium Catalysis2.1.2 Nickel

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12

Seidl, Frederick J., and Noah Z. Burns. "Selective bromochlorination of a homoallylic alcohol for the total synthesis of (−)-anverene." Beilstein Journal of Organic Chemistry 12 (July 1, 2016): 1361–65. http://dx.doi.org/10.3762/bjoc.12.129.

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The scope of a recently reported method for the catalytic enantioselective bromochlorination of allylic alcohols is expanded to include a specific homoallylic alcohol. Critical factors for optimization of this reaction are highlighted. The utility of the product bromochloride is demonstrated by the first total synthesis of an antibacterial polyhalogenated monoterpene, (−)-anverene.

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13

Marshall, James A., and Robert C. Andrews. "Coupling of allylic alcohol epoxides with sulfur-stabilized allylic anions." Journal of Organic Chemistry 50, no. 10 (1985): 1602–6. http://dx.doi.org/10.1021/jo00210a009.

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14

Urlacher, Vlada B., and Katja Koschorreck. "Pecularities and applications of aryl-alcohol oxidases from fungi." Applied Microbiology and Biotechnology 105, no. 10 (2021): 4111–26. http://dx.doi.org/10.1007/s00253-021-11337-4.

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Abstract Aryl-alcohol oxidases (AAOs) are FAD-containing enzymes that oxidize a broad range of aromatic as well as aliphatic allylic alcohols to aldehydes. Their broad substrate spectrum accompanied by the only need for molecular oxygen as cosubstrate and production of hydrogen peroxide as sole by-product makes these enzymes very promising biocatalysts. AAOs were used in the synthesis of flavors, fragrances, and other high-value-added compounds and building blocks as well as in dye decolorization and pulp biobleaching. Furthermore, AAOs offer a huge potential as efficient suppliers of hydrogen

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15

Yuasa, Akihiro, Kazunori Nagao та Hirohisa Ohmiya. "Allylic cross-coupling using aromatic aldehydes as α-alkoxyalkyl anions". Beilstein Journal of Organic Chemistry 16 (7 лютого 2020): 185–89. http://dx.doi.org/10.3762/bjoc.16.21.

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The allylic cross-coupling using aromatic aldehydes as α-alkoxyalkyl anions is described. The synergistic palladium/copper-catalyzed reaction of aromatic aldehydes, allylic carbonates, and a silylboronate produces the corresponding homoallylic alcohol derivatives. This process involves the catalytic formation of a nucleophilic α-silyloxybenzylcopper(I) species and the subsequent palladium-catalyzed allylic substitution.

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16

Altamore, Timothy M., Oanh T. K. Nguyen, Quentin I. Churches, et al. "Concise Synthesis of Enantiomerically Pure (1'S,2'R)- and (1'R,2'S)-2S-Amino-3-(2'-aminomethyl-cyclopropyl)propionic Acid: Two E-Diastereoisomers of 4,5-Methano-L-lysine." Australian Journal of Chemistry 66, no. 9 (2013): 1105. http://dx.doi.org/10.1071/ch13309.

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A concise synthesis of both E-isomers of 2S-amino-3-(2′-aminomethyl-cyclopropyl)propionic acid, new methano-l-lysines, is described. The synthetic route includes nine steps from l-methionine, with a key step involving the cyclopropanation of an intermediate E-allylic alcohol. The resultant hydroxymethylcyclopropanes were readily separated and converted into the title α-amino acids. The stereochemistry around the cyclopropane rings was deduced by conducting the cyclopropanation in the presence of N,N,N′,N′-tetramethyl-d-tartaric acid diamide butylboronate, a chiral controller which is known to

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17

Ma, Xinghua, Natasha Anderson, Lorenzo V. White, et al. "The Conversion of Levoglucosenone into Isolevoglucosenone." Australian Journal of Chemistry 68, no. 4 (2015): 593. http://dx.doi.org/10.1071/ch14574.

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Levoglucosenone (1), a compound that will soon be available in tonne quantities through the pyrolysis of acid-treated lignocellulosic biomass, has been converted into isolevoglucosenone (2) using Wharton rearrangement chemistry. Treatment of compound 1 with alkaline hydrogen peroxide gave the γ-lactones 5 and 6 rather than the required epoxy-ketones 3 and/or 4. However, the latter pair of compounds could be obtained by an initial Luche reduction of compound 1, electrophilic epoxidation of the resulting allylic alcohol 8 and oxidation of the product oxiranes 9 and 10. Independent treatment of c

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18

Pakulski, Zbigniew, Norbert Gajda, Magdalena Jawiczuk, Jadwiga Frelek, Piotr Cmoch, and Sławomir Jarosz. "Synthesis of a sucrose dimer with enone tether; a study on its functionalization." Beilstein Journal of Organic Chemistry 10 (May 28, 2014): 1246–54. http://dx.doi.org/10.3762/bjoc.10.124.

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The reaction of appropriately functionalized sucrose phosphonate with sucrose aldehyde afforded a dimer composed of two sucrose units connected via their C6-positions (‘the glucose ends’). The carbonyl group in this product (enone) was stereoselectively reduced with zinc borohydride and the double bond (after protection of the allylic alcohol formed after reduction) was oxidized with osmium tetroxide to a diol. Absolute configurations of the allylic alcohol as well as the diol were determined by circular dichroism (CD) spectroscopy using the in situ dimolybdenum methodology.

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19

Kobayashi, Yuichi. "Coupling Reactions on Secondary Allylic, Propargylic, and Alkyl Carbons Using Organoborates/Ni and RMgX/Cu Reagents." Catalysts 13, no. 1 (2023): 132. http://dx.doi.org/10.3390/catal13010132.

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In the first part of this review, secondary carbon-carbon bond formation by using allylic coupling reactions with aryl and alkenyl borates is presented. Early investigations have revealed the suitability of a nickel catalyst and [RTB(OMe)3]Li (RT: transferable group). Due to their low reactivity, the borates were converted to more reactive congeners possessing an alkanediol ligand, such as 2,3-butanediol and 2,2-dimethyl-1,3-propanediol. Borates with such diol ligands were used to install aryl and alkenyl groups on the monoacetate of 4-cyclopentenyl-1,3-diol. Furthermore, alkenyl borates showe

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20

Wang, Jingjing, Samuel Z. Y. Ting, and Joanne E. Harvey. "Preparation of conjugated dienoates with Bestmann ylide: Towards the synthesis of zampanolide and dactylolide using a facile linchpin approach." Beilstein Journal of Organic Chemistry 11 (October 5, 2015): 1815–22. http://dx.doi.org/10.3762/bjoc.11.197.

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Bestmann ylide [(triphenylphosphoranylidene)ketene] acts as a chemical linchpin that links nucleophilic entities, such as alcohols or amines, with carbonyl moieties to produce unsaturated esters and amides, respectively. In this work, the formation of α,β,γ,δ-unsaturated esters (dienoates) is achieved through the coupling of Bestmann ylide, an alcohol and an α,β-unsaturated aldehyde. Primary and secondary alcohols, including allylic alcohols, are suitable substrates; the newly formed alkene has an E-geometry. Strategically, this represents a highly efficient route to unsaturated polyketide der

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21

Hoye, Thomas R., and Hongyu Zhao. "Some Allylic Substituent Effects in Ring-Closing Metathesis Reactions: Allylic Alcohol Activation." Organic Letters 1, no. 7 (1999): 1123–25. http://dx.doi.org/10.1021/ol990947+.

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22

Tait, Katrina, Samuel Koh, Nicolas Blanchard, and William Tam. "Ruthenium-catalyzed ring-opening reaction of a 3-aza-2-oxabicyclo[2.2.1]hept-5-ene with amines — an unexpected mode of ring-opening." Canadian Journal of Chemistry 97, no. 4 (2019): 310–16. http://dx.doi.org/10.1139/cjc-2018-0444.

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The ruthenium-catalyzed ring-opening reaction of a 3-aza-2-oxabicyclo[2.2.1]hept-5-ene with amines was investigated. In the presence of an amine and a ruthenium catalyst, the N–O bond is cleaved, forming a ring-opened allylic alcohol product. Through a possible ruthenium-catalyzed redox isomerization, the allylic alcohol is transformed into a saturated carbonyl product. This unexpected mode of ruthenium-catalyzed ring-opening reaction of a 3-aza-2-oxabicyclo[2.2.1]hept-5-ene leads to the formation of a cyclopentanone derivative in moderate yields.

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23

Malone, Vincent F., Amy J. Chastain, John T. Ohlsson, Loelle S. Poneleit, Michele Nemecek-Marshall, and Ray Fall. "Characterization of a Pseudomonas putidaAllylic Alcohol Dehydrogenase Induced by Growth on 2-Methyl-3-Buten-2-ol." Applied and Environmental Microbiology 65, no. 6 (1999): 2622–30. http://dx.doi.org/10.1128/aem.65.6.2622-2630.1999.

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ABSTRACT We have been working to develop an enzymatic assay for the alcohol 2-methyl-3-buten-2-ol (232-MB), which is produced and emitted by certain pines. To this end we have isolated the soil bacteriumPseudomonas putida MB-1, which uses 232-MB as a sole carbon source. Strain MB-1 contains inducible 3-methyl-2-buten-1-ol (321-MB) and 3-methyl-2-buten-1-al dehydrogenases, suggesting that 232-MB is metabolized by isomerization to 321-MB followed by oxidation. 321-MB dehydrogenase was purified to near-homogeneity and found to be a tetramer (151 kDa) with a subunit mass of 37,700 Da. It catalyzes

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24

Kohr, Michael, and Uli Kazmaier. "Halogenated Allyl Alcohol Derivatives - Versatile Electrophiles for Palladium-Catalyzed Allylic Alkylations." European Journal of Organic Chemistry 2019, no. 17 (2019): 2843–49. http://dx.doi.org/10.1002/ejoc.201900310.

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25

Shukla, Vilas B., and Pushpa R. Kulkarni. "Production of allyl phenyl carbinol (APC) by biotrans-formation using Rhizopus arrhizus." Brazilian Archives of Biology and Technology 43, no. 3 (2000): 249–52. http://dx.doi.org/10.1590/s1516-89132000000300001.

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The objective of the present work was to study the stereoselective synthesis of homo-allylic alcohol using stereoselective hydrolysis by Rhizopus arrhizus and also to study the stereoselective synthesis of allyl phenyl carbinol (APC) or 1-Phenyl-3-butene-1-o by combination of chemical synthesis and biotransformation from cheap raw materials such as benzaldehyde and allyl bromide. Stereospecific synthesis of allyl phenyl carbinol (APC) was achieved by acetate hydrolysis by R. arrhizus giving R (+) enantiomer. Maximum enantiomeric excess of APC was obtained at 16 h where as maximum yield of it w

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26

Leung, Dennis H., Robert G. Bergman, and Kenneth N. Raymond. "Highly Selective Supramolecular Catalyzed Allylic Alcohol Isomerization." Journal of the American Chemical Society 129, no. 10 (2007): 2746–47. http://dx.doi.org/10.1021/ja068688o.

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27

Tanaka, Shinji, Masato Kitamura, Shoutaro Iwase, Sena Kanda, Marie Kato, and Yutaro Kiriyama. "Ruthenium-Catalyzed Asymmetric Dehydrative Allylic Cyclization of Five-Membered Chalcogen Heteroaromatics." Synthesis 53, no. 17 (2021): 3121–25. http://dx.doi.org/10.1055/a-1523-6826.

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AbstractThe asymmetric dehydrative intramolecular allylation reactions of furan and thiophene were performed using a cationic cyclopentadienyl-ruthenium (CpRu) complex of a chiral pyridine carboxylic acid, namely Cl-Naph-PyCOOH. Both furan and thiophene tethered with an allylic alcohol gave the corresponding bicyclic compounds in high yields and enantioselectivities using 0.1–5 mol% of the catalyst. The reaction was found to proceed via a similar enantioface selection mechanism to that previously reported by our group, which involved halogen and hydrogen bond formation, in addition to the gene

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28

Hu, Jiadong, Dongyang Xu, Qiang Zhang, et al. "Tandem allylic alcohol isomerization/oxo-Michael addition reaction promoted by Re2O7." RSC Advances 6, no. 58 (2016): 52583–86. http://dx.doi.org/10.1039/c6ra10399e.

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29

Khedher, I., A. Ghorbel, and A. Tuel. "Physicochemical Properties of Vanadium-Containing Montmorillonite in Epoxidation of Allylic Alcohol." Journal of Chemical Research 2003, no. 7 (2003): 390–94. http://dx.doi.org/10.3184/030823403103174515.

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Vanadium-containing aluminosilicate molecule sieves were observed to exhibit remarkable catalytic activity in oxidation of hydrocarbons, notably epoxidation of allylic alcohol. In this paper, we review the spectroscopic characterisation of framework incorporation and redox behavior of vanadium in both natural montmorillonite and K10. NMR and EPR studies of coordination and oxidation state of vanadium in dried and calcined samples show that vanadium exists mainly in a tetrahedral oxygen coordination as an isolated monomeric state (VO43-) in V-mont and also as dimeric state [O3V-O-VO3]2- in V-K1

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30

Hitrik, Maria, Anirban Dandapat, and Yoel Sasson. "A new mechanism for allylic alcohol isomerization involving ruthenium nanoparticles as a ‘true catalyst’ generated through the self-assembly of supramolecular triruthenium clusters." RSC Advances 6, no. 72 (2016): 68041–48. http://dx.doi.org/10.1039/c6ra14658a.

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31

Brown, William L., and Alex G. Fallis. "Intramolecular rearrangements: Epimerization of bicyclic vinyl tertiary alcohols via a [2,3] sulfoxide sigmatropic rearrangement." Canadian Journal of Chemistry 65, no. 8 (1987): 1828–32. http://dx.doi.org/10.1139/v87-307.

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A general method for inverting the stereochemistry of bicyclic vinyl endo alcohols such as 6 and 12 to give the corresponding exo isomers 10 and 18 is described. The procedures employ a [2,3] sulfoxide rearrangement as a key step. In the case of the norbornene alcohol 12 the intermediate sulfenate ester 13 gives the oxetane 14 rather than the expected sulfoxide 17. It was therefore prepared by thionyl chloride induced rearrangement of 12 to the allylic chloride 15 followed by displacement (PhSNa) and oxidation (m-chloroperbenzoic acid). The exo alcohol thus obtained underwent smooth anionic ox

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32

Dethe, Dattatraya H., Rohan D. Erande, Samarpita Mahapatra, Saikat Das, and Vijay Kumar B. "Protecting group free enantiospecific total syntheses of structurally diverse natural products of the tetrahydrocannabinoid family." Chemical Communications 51, no. 14 (2015): 2871–73. http://dx.doi.org/10.1039/c4cc08562k.

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33

Liu, Shengnan, Jianbiao Liu, Qiong Wang, et al. "The origin of regioselectivity in Cu-catalyzed hydrocarbonylative coupling of alkynes with alkyl halides." Organic Chemistry Frontiers 7, no. 9 (2020): 1137–48. http://dx.doi.org/10.1039/d0qo00214c.

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34

Aldrich, Leslie, Qiwen Gao, Lianyan Xu, Vincent Parise, and Yash Mehta. "Enantioselective Synthesis of 4-Amino-3-hydroxybenzopyran Flavanol Derivatives from Chalcones." Synthesis 50, no. 24 (2018): 4796–808. http://dx.doi.org/10.1055/s-0037-161114.

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A concise method that is easily amenable for analogue synthesis has been developed to enantioselectively access 4-amino-3-hydroxybenzopyrans from chalcones. Epoxy alcohols were formed from chalcones through a Corey–Bakshi–Shibata reduction of the enone and subsequent Sharpless asymmetric epoxidation of the allylic alcohol. The epoxy alcohols were protected, regioselectively opened with various amines using catalytic europium(III) triflate, and the resulting free alcohols were orthogonally protected. Concomitant deprotection and intramolecular nucleophilic aromatic substitution provided the ben

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35

Zheng, Meifang, Pengquan Chen, Wanqing Wu, and Huanfeng Jiang. "Palladium-catalyzed Heck-type reaction of oximes with allylic alcohols: synthesis of pyridines and azafluorenones." Chemical Communications 52, no. 1 (2016): 84–87. http://dx.doi.org/10.1039/c5cc06958k.

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36

Hodgson, David M., та Rosanne S. D. Persaud. "Alkenes from β-lithiooxyphosphonium ylides generated by trapping α-lithiated terminal epoxides with triphenylphosphine". Beilstein Journal of Organic Chemistry 8 (7 листопада 2012): 1896–900. http://dx.doi.org/10.3762/bjoc.8.219.

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Terminal epoxides undergo lithium 2,2,6,6-tetramethylpiperidide-induced α-lithiation and subsequent interception with Ph3P to provide a new and direct entry to β-lithiooxyphosphonium ylides. The intermediacy of such an ylide is demonstrated by representative alkene-forming reactions with chloromethyl pivalate, benzaldehyde and CD3OD, giving a Z-allylic pivalate, a conjugated E-allylic alcohol and a partially deuterated terminal alkene, respectively, in modest yields.

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37

Szechner, Barbara, and Osman Achmatowicz. "Total Synthesis of Protected Form of Fungi Metabolite Cortalcerone." Collection of Czechoslovak Chemical Communications 57, no. 1 (1992): 159–68. http://dx.doi.org/10.1135/cccc19920159.

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Synthesis of methyl 4,5-dideoxy-D,L-hex-4-enos-2-ulopyranosid-3-ulose ethylene acetal, derivative of the first natural sugar with dihydropyranone moiety, from 5-acetoxymethylfurfural is described. It was shown that 1,3-transposition of the allylic alcohol in the dihydropyran ring, a key step of the synthesis, can be carried out via an intermediate allylic selenoxide with excellent regio- and stereoselectivity.

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38

Wang, Ge, Ampa Jimtaisong, and Rudy L. Luck. "Allylic Alcohol Isomerization and Mechanistic Considerations with CH3ReO3." Organometallics 23, no. 19 (2004): 4522–25. http://dx.doi.org/10.1021/om049669v.

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39

Fleming, Ian, and Andrew P. Thomas. "Regiocontrolled allylsilane synthesis from secondary allylic alcohol derivatives." Journal of the Chemical Society, Chemical Communications, no. 7 (1985): 411. http://dx.doi.org/10.1039/c39850000411.

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40

Kallatsa, Oili A., and Ari M. P. Koskinen. "Anti-Kishi selective dihydroxylation of allylic alcohol derivatives." Tetrahedron Letters 38, no. 51 (1997): 8895–98. http://dx.doi.org/10.1016/s0040-4039(97)10350-1.

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41

Saito, Shun, Takashi Yamazaki, and Yuichi Kobayashi. "Stereoselective ozonolysis of TMS-substituted allylic alcohol derivatives and synthesis of 14R,15S- and 14S,15S-diHETE." Organic & Biomolecular Chemistry 16, no. 41 (2018): 7636–47. http://dx.doi.org/10.1039/c8ob02116c.

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42

Hirata, Goki, Hideaki Satomura, Hidenobu Kumagae, Aika Shimizu, Gen Onodera, and Masanari Kimura. "Direct Allylic Amination of Allylic Alcohol Catalyzed by Palladium Complex Bearing Phosphine–Borane Ligand." Organic Letters 19, no. 22 (2017): 6148–51. http://dx.doi.org/10.1021/acs.orglett.7b03023.

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43

Hoye, Thomas R., and Hongyu Zhao. "ChemInform Abstract: Some Allylic Substituent Effects in Ring-Closing Metathesis Reactions: Allylic Alcohol Activation." ChemInform 30, no. 52 (2010): no. http://dx.doi.org/10.1002/chin.199952088.

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44

Mosa, Fathia A., and Andrew Whiting. "A Facile Autoxidation of an Allylic Alcohol in Air." International Letters of Chemistry, Physics and Astronomy 83 (August 2019): 41–47. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.83.41.

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Abstract:

An (4E,6E)-alkadienyl alcohol which is a solid compound which can be stored at rt, upon dissolving into a suitable solvent undergoes facile autoxidation (4E,6E)-alkadienyl alcohol 1 in air at room temperature. The result is complete decompose leading to a mixture of products, including benzaldehyde (24%) and cinnamaldehyde (29%). Possible mechanistic explanations for the autoxidation are discussed.

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45

Mosa, Fathia A., and Andrew Whiting. "A Facile Autoxidation of an Allylic Alcohol in Air." International Letters of Chemistry, Physics and Astronomy 83 (August 14, 2019): 41–47. http://dx.doi.org/10.56431/p-f37ga2.

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Abstract:

An (4E,6E)-alkadienyl alcohol which is a solid compound which can be stored at rt, upon dissolving into a suitable solvent undergoes facile autoxidation (4E,6E)-alkadienyl alcohol 1 in air at room temperature. The result is complete decompose leading to a mixture of products, including benzaldehyde (24%) and cinnamaldehyde (29%). Possible mechanistic explanations for the autoxidation are discussed.

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46

Hensienne, Raphaël, Jean-Philippe Cusson, Étienne Chénard та Stephen Hanessian. "Catalytic Lewis and Brønsted acid syn-diastereoselective benzylic substitutions of α-hydroxy-β-nitro- and α-hydroxy-β-azido-alkyl arenes". Canadian Journal of Chemistry 98, № 6 (2020): 292–306. http://dx.doi.org/10.1139/cjc-2020-0016.

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A series of alkyl and alkenyl p-methoxy arenes containing α,β-disubstituted diamino and amino alcohol groups were synthesized from β-nitro and β-azido benzylic alcohols in the presence of AuCl3 as catalyst. The formation of predominantly syn-disubstituted products were rationalized on the basis of mechanistic considerations and transition state models relying on A1,3-allylic strain. The products could have utility in the design of medicinally relevant compounds and as chiral ligands for asymmetric catalysis. A new synthesis of (+)-sertraline (Zoloft) was achieved.

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Sheng, Shou-Ri, and Xian Huang. "Synthesis of Allylic Esters and Ethers Using Polymer-Supported Selenium Bromide." Journal of Chemical Research 2002, no. 4 (2002): 184–85. http://dx.doi.org/10.3184/030823402103171609.

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The treatment of adducts from polymer-supported selenium bromide on olefins with anhydrous carboxylate or alcohol and oxidation of the resulting products afford allylic esters and ethers in good yield and purity.

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Sølvhøj, Amanda, Esben Taarning, and Robert Madsen. "Methyl vinyl glycolate as a diverse platform molecule." Green Chemistry 18, no. 20 (2016): 5448–55. http://dx.doi.org/10.1039/c6gc01556e.

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Methyl vinyl glycolate (MVG) is available by zeolite catalyzed degradation of sugars and constitutes a precursor to industrially promising structures by homo metathesis, cross metathesis, Claisen-type rearrangements and allylic alcohol transposition.

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Yamamoto, Y., T. Kurohara, and M. Shibuya. "CF3-Substituted semisquarate: a pluripotent building block for the divergent synthesis of trifluoromethylated functional molecules." Chemical Communications 51, no. 91 (2015): 16357–60. http://dx.doi.org/10.1039/c5cc06920c.

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The first synthesis of a CF<sub>3</sub>-substituted semisquarate was accomplished via nucleophilic trifluoromethylation using CF<sub>3</sub>SiMe<sub>3</sub> and subsequent rhenium-catalyzed allylic alcohol rearrangement.

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Wang, Ze-Shu, Yang-Bo Chen, Kun Wang, Zhou Xu, and Long-Wu Ye. "One-pot synthesis of 2-hydroxymethylindoles via photoredox-catalyzed ketyl–ynamide coupling/1,3-allylic alcohol transposition." Green Chemistry 22, no. 14 (2020): 4483–88. http://dx.doi.org/10.1039/d0gc01522a.

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An efficient photoredox-catalyzed ketyl–ynamide coupling of alkyl sulfonyl substituted ynamides followed by 1,3-allylic alcohol transposition in one-pot has been developed, affording 2-hydroxymethylindoles in generally moderate to good yields.

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