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Journal articles on the topic 'Β-amino alcohols'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Leemans, Laura, Marc D. Walter, Frank Hollmann, Anett Schallmey, and Luuk M. van Langen. "Multi-Catalytic Route for the Synthesis of (S)-Tembamide." Catalysts 9, no. 10 (2019): 822. http://dx.doi.org/10.3390/catal9100822.

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Enantiopure β-amino alcohols constitute one of the most significant building blocks for the synthesis of active pharmaceutical ingredients. Despite the availability of a range of chiral β-amino alcohols from a chiral pool, there is a growing demand for new enantioselective synthetic routes to vicinal amino alcohols and their derivatives. In the present study, an asymmetric 2-step catalytic route that converts 4-anisaldehyde into a β-amino alcohol derivative, (S)-tembamide, with excellent enantiopurity (98% enantiomeric excess) has been developed. The recently published initial step consists in

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2

Du, Li-Hua, Miao Xue, Meng-Jie Yang та ін. "Ring-Opening of Epoxides with Amines for Synthesis of β-Amino Alcohols in a Continuous-Flow Biocatalysis System". Catalysts 10, № 12 (2020): 1419. http://dx.doi.org/10.3390/catal10121419.

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An efficient method for the preparation of β-amino alcohols catalyzed by lipase TL IM from Thermomyces lanuginosus in a continuous-flow reactor was developed. The eco-friendly biocatalyst combined with continuous-flow reaction technology displayed high efficiency in the synthesis of β-amino alcohols. The benign reaction conditions (35 °C) and short residence time (20 min), together with the use of low cost and readily available starting materials, make this synthetic approach a promising alternative to current β-amino alcohol synthesis.

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3

Kang, Taek, Heejeong Kim, Jeung Gon Kim, and Sukbok Chang. "Synthesis of 1,2-amino alcohols via catalytic C–H amidation of sp3 methyl C–H bonds." Chem. Commun. 50, no. 81 (2014): 12073–75. http://dx.doi.org/10.1039/c4cc05655h.

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A new route to 1,2-amino alcohols is presented by C–H amidation of sp<sup>3</sup> methyl C–H bonds as a key step. Various alcohols were employed after converting them to removable ketoxime chelating groups. Iridium-catalyzed C–H amidation and following LAH reduction furnished β-amino alcohol products.

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4

Hosseini-Sarvari, Mona. "Synthesis of β-amino alcohols using MgO as a new catalyst under solvent-free conditions". Canadian Journal of Chemistry 86, № 1 (2008): 65–71. http://dx.doi.org/10.1139/v07-135.

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MgO catalyzed efficiently the ring opening of epoxides with a range of aromatic and aliphatic amines to produce β-substituted alcohols in high yields under solvent-free conditions. Exclusive trans stereoselectivity is observed for cyclic epoxide.Key words: MgO, β-amino alcohols, solvent-free, epoxide, amine.

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5

Wang, Hongyue, Ge Qu, Jun-Kuan Li, et al. "Data mining of amine dehydrogenases for the synthesis of enantiopure amino alcohols." Catalysis Science & Technology 10, no. 17 (2020): 5945–52. http://dx.doi.org/10.1039/d0cy01373k.

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Five amine dehydrogenases (AmDHs) derived from amino acid dehydrogenases have been identified and evaluated for the stereoselective amination of α-/β-functionalized carbonyl compounds to synthesize chiral amino alcohols.

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6

Rossi, Bianca, Nadia Pastori, Simona Prosperini та Carlo Punta. "Multicomponent versus domino reactions: One-pot free-radical synthesis of β-amino-ethers and β-amino-alcohols". Beilstein Journal of Organic Chemistry 11 (15 січня 2015): 66–73. http://dx.doi.org/10.3762/bjoc.11.10.

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Following an optimized multicomponent procedure, an aryl amine, a ketone, and a cyclic ether or an alcohol molecule are assembled in a one-pot synthesis by nucleophilic radical addition of ketyl radicals to ketimines generated in situ. The reaction occurs under mild conditions by mediation of the TiCl4/Zn/t-BuOOH system, leading to the formation of quaternary β-amino-ethers and -alcohols. The new reaction conditions guarantee good selectivity by preventing the formation of secondary products. The secondary products are possibly derived from a competitive domino reaction, which involves further

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7

Chevis, Philip J., Thanika Promchai, Christopher Richardson, Thunwadee Limtharakul та Stephen G. Pyne. "Synthesis of syn- and enantioenriched anti-β-amino alcohols by highly diastereoselective borono-Mannich allylation reactions". Chemical Communications 58, № 13 (2022): 2220–23. http://dx.doi.org/10.1039/d1cc06775c.

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A highly diastereoselective method for the synthesis of syn-β-amino alcohols and enantioenriched anti-β-amino alcohols has been developed involving α-hydroxyl aldehydes and chiral α-phenylaminoxyaldehydes or α-benzoyloxyaldehydes, respectively in Petasis borono-Mannich allylation reactions.

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8

Aschwanden, Patrick, Lisbet Kværnø, Roger W. Geisser, Florian Kleinbeck та Erick M. Carreira. "Reduction of 2,3-Dihydroisoxazoles to β-Amino Ketones and β-Amino Alcohols". Organic Letters 7, № 25 (2005): 5741–42. http://dx.doi.org/10.1021/ol052540c.

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9

Wosińska-Hrydczuk, Marzena, and Jacek Skarżewski. "2-Oxiranyl-pyridines: Synthesis and Regioselective Epoxide Ring Openings with Chiral Amines as a Route to Chiral Ligands." Heteroatom Chemistry 2019 (October 9, 2019): 1–12. http://dx.doi.org/10.1155/2019/2381208.

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New epoxides, derivatives of pyridine, 2,2′-bipyridine, and 1,10-phenanthroline, were synthesized from the respective α-methylazaarenes. The obtained racemic 2-oxiranyl-azaarenes along with styrene oxide and trans-stilbene oxide were submitted to the ring opening with chiral primary amines as a chiral auxiliary. The most effective reaction was run in the presence of Sc(OTf)3/diisopropylethylamine for 7 days at 80°C, affording a good yield of the amino alcohols. Except for styrene oxide which gave both α- and β-amino alcohols, the reactions led regioselectively to the corresponding diastereomer

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10

Cossar, Peter J., Jennifer R. Baker, Nicholas Cain та Adam McCluskey. "In situ epoxide generation by dimethyldioxirane oxidation and the use of epichlorohydrin in the flow synthesis of a library of β-amino alcohols". Royal Society Open Science 5, № 4 (2018): 171190. http://dx.doi.org/10.1098/rsos.171190.

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The flow coupling of epichlorohydrin with substituted phenols, while efficient, limits the nature of the epoxide available for the development of focused libraries of β-amino alcohols. This limitation was encountered in the production of analogues of 1-(4-nitrophenoxy)-3-((2-((4-(trifluoromethyl)pyrimidin-2-yl)amino)ethyl)amino)propan-2-ol 1 , a potential antibiotic lead. The in situ (flow) generation of dimethyldoxirane (DMDO) and subsequent flow olefin epoxidation abrogates this limitation and afforded facile access to structurally diverse β-amino alcohols. Analogues of 1 were readily access

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11

Wosińska-Hrydczuk, Marzena, Przemysław J. Boratyński та Jacek Skarżewski. "Regioselective and Stereodivergent Synthesis of Enantiomerically Pure Vic-Diamines from Chiral β-Amino Alcohols with 2-Pyridyl and 6-(2,2′-Bipyridyl) Moieties". Molecules 25, № 3 (2020): 727. http://dx.doi.org/10.3390/molecules25030727.

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In this report, we describe the synthetic elaboration of the easily available enantiomerically pure β-amino alcohols. Attempted direct substitution of the hydroxyl group by azido-functionality in the Mitsunobu reaction with hydrazoic acid was inefficient or led to a diastereomeric mixture. These outcomes resulted from the participation of aziridines. Intentionally performed internal Mitsunobu reaction of β-amino alcohols gave eight chiral aziridines in 45–82% yield. The structural and configuration identity of products was confirmed by NMR data compared to the DFT calculated GIAO values. For 1

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12

Fadlalla, Mohamed, Glenn Maguire, and Holger Friedrich. "The Heterogeneous Aminohydroxylation Reaction Using Hydrotalcite-Like Catalysts Containing Osmium." Catalysts 8, no. 11 (2018): 547. http://dx.doi.org/10.3390/catal8110547.

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The aminohydroxylation reaction of olefins is a key organic transformation reaction, typically carried out homogeneously with toxic and expensive osmium (Os) catalysts. Therefore, heterogenisation of this reaction can unlock its industrial potential by allowing reusability of the catalyst. Os–Zn–Al hydrotalcite-like compounds (HTlcs), as potential heterogeneous aminohydroxylation catalysts, were synthesised by the co-precipitation method and characterised by several techniques. Reaction parameters (i.e., solvent system, reaction temperature, and catalyst structure) were optimized with cyclohex

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13

Zhao, Hai-Ying, Zhan-Xi Bian та Bao-Guo Li. "Synthesis of β-amino-α-ferrocenyl alcohols". Journal of Chemical Research 2005, № 11 (2005): 712–15. http://dx.doi.org/10.3184/030823405774909351.

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β-Amino-α-ferrocenyl alcohols [FcC(OH)(R)CH2NH2] (R = Me, Et, nPr, iPr, Ph, p-MeOC6H4, o-ClC6H4, m-ClC6H4, p-ClC6H4, Fc; Fc = C5H4FeC5H5) were prepared by the reduction of cyanohydrin trimethylsilyl ethers of acylferrocenes with lithium aluminum hydride. All new compounds were characterised by elemental analysis, IR and 1H NMR spectroscopies. The X-ray crystal structure of β-amino-α,α-diferrocenylethanol shows that it has a polymeric chain structure with hydrogen bonding interactions between the OH proton and the N of NH2.

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14

Lee, Hee-Seung, та Sung Ho Kang. "Synthesis of Physiologically Potent β-Amino Alcohols". Synlett, № 10 (2004): 1673–85. http://dx.doi.org/10.1055/s-2004-829578.

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15

Job, Gabriel E., та Stephen L. Buchwald. "Copper-Catalyzed Arylation of β-Amino Alcohols". Organic Letters 4, № 21 (2002): 3703–6. http://dx.doi.org/10.1021/ol026655h.

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16

Métro, Thomas-Xavier, Jérôme Appenzeller, Domingo Gomez Pardo та Janine Cossy. "Highly Enantioselective Synthesis of β-Amino Alcohols". Organic Letters 8, № 16 (2006): 3509–12. http://dx.doi.org/10.1021/ol061133d.

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17

Barrett, Anthony G. M., Mark A. Seefeld, Andrew J. P. White та David J. Williams. "Convenient Asymmetric Syntheses ofanti-β-Amino Alcohols". Journal of Organic Chemistry 61, № 8 (1996): 2677–85. http://dx.doi.org/10.1021/jo9522062.

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18

Teixeira, Cláudia, Renato B. Pereira, Nuno F. S. Pinto та ін. "Eugenol β-Amino/β-Alkoxy Alcohols with Selective Anticancer Activity". International Journal of Molecular Sciences 23, № 7 (2022): 3759. http://dx.doi.org/10.3390/ijms23073759.

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Eugenol, 4-allyl-2-methoxyphenol, is the main constituent of clove essential oil and has demonstrated relevant biological activity, namely anticancer activity. Aiming to increase this activity, we synthesized a series of eugenol β-amino alcohol and β-alkoxy alcohol derivatives, which were then tested against two human cancer cell lines, namely gastric adenocarcinoma cells (AGS) and lung adenocarcinoma cells (A549). An initial screening was performed to identify the most cytotoxic compounds. The results demonstrated that three β-amino alcohol derivatives had anticancer activity that justified s

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19

Bravo, Pierfrancesco, Marcello Crucianelli, Taizo Ono та Matteo Zanda. "Synthesis and biological activity of β-fluoroalkyl β-amino alcohols". Journal of Fluorine Chemistry 97, № 1-2 (1999): 27–49. http://dx.doi.org/10.1016/s0022-1139(99)00024-x.

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20

Petrova, Polina A., Denis V. Sudarikov, Larisa L. Frolova, Roman V. Rumyantcev, Svetlana A. Rubtsova, and Aleksandr V. Kutchin. "Synthesis of Trifluoromethylated Monoterpene Amino Alcohols." Molecules 27, no. 20 (2022): 7068. http://dx.doi.org/10.3390/molecules27207068.

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For the first time, monoterpene trifluoromethylated β-hydroxy-benzyl-O-oximes were synthesized in 81–95% yields by nucleophilic addition of the Ruppert–Prakash reagent (TMSCF3) to the corresponding β-keto-benzyl-O-oximes based on (+)-nopinone, (−)-verbanone and (+)-camphoroquinone. Trifluoromethylation has been determined to entirely proceed chemo- and stereoselective at the C=O rather than C=N bond. Trifluoromethylated benzyl-O-oximes were reduced to the corresponding α-trifluoromethyl-β-amino alcohols in 82–88% yields. The structure and configuration of the compounds obtained have been estab

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21

Gourhari, Maiti, Kundu Pradip та K. Mallik Asok. "Mild and efficient synthesis of β-amino alcohols by antimony trichloride catalysed opening of epoxides". Journal of Indian Chemical Society Vol. 85, Apr 2008 (2008): 412–16. https://doi.org/10.5281/zenodo.5814946.

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Department of Chemistry, Jadavpur University, Jadavpur, Kolkata-700 032, India E-mail : ghmaiti123@yahoo.co.in        Fax : 91-33-24146223 Manuscript received 14 December 2007, accepted 3 January 2008 Nucleophilic opening or epoxides with aniline derivatives in the presence of catalytic amount or anthnony trichloride in acetonitrile at room temperature afford the corresponding β-amino alcohols in excellent to very good yield.

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22

Rehdorf, Jessica, Marko D Mihovilovic, Marco W Fraaije та Uwe T Bornscheuer. "Enzymatic Synthesis of Enantiomerically Pure β-Amino Ketones, β-Amino Esters, and β-Amino Alcohols with Baeyer-Villiger Monooxygenases". Chemistry - A European Journal 16, № 31 (2010): 9525–35. http://dx.doi.org/10.1002/chem.201001480.

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23

Kasprzyk, Wiktor, Szczepan Bednarz, Paweł Żmudzki, Mateusz Galica, and Dariusz Bogdał. "Novel efficient fluorophores synthesized from citric acid." RSC Advances 5, no. 44 (2015): 34795–99. http://dx.doi.org/10.1039/c5ra03226a.

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Citric acid was reacted with α,β-diamines, β-amino thiols and β-amino alcohols to produce fluorescent derivatives of 2-pyridone (QY up to ∼79%). The chemical structures of these compounds were confirmed by analyses of 1D, 2D NMR and ESI-MS data.

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24

Nomura, Miku, Zubeda Begum, Chigusa Seki та ін. "Thiourea fused γ-amino alcohol organocatalysts for asymmetric Mannich reaction of β-keto active methylene compounds with imines". RSC Advances 13, № 6 (2023): 3715–22. http://dx.doi.org/10.1039/d2ra08317e.

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Catalytic functionality of new optically active thiourea fused γ-amino alcohols was examined in the asymmetric Mannich reaction of β-keto active methylene compounds with imines to afford chiral Mannich products, β-amino keto compounds..

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25

Tak, Raj Kumar, Manish Kumar, Mohd Nazish, Tushar Kumar Menapara, Rukhsana I. Kureshy, and Noor-ul H. Khan. "Development of recyclable chiral macrocyclic metal complexes for asymmetric aminolysis of epoxides: application for the synthesis of an enantiopure oxazolidine ring." New Journal of Chemistry 42, no. 18 (2018): 15325–31. http://dx.doi.org/10.1039/c8nj02960a.

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Macrocyclic Cr(iii)-salen complexes were synthesized for the ring opening reaction of various epoxides with anilines to furnish the corresponding β-amino-α-hydroxyl esters and β-amino alcohols with excellent ee/yield upto 99/95%.

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26

Szönyi, S., A. Ayari, M. Nasreddine та A. Cambon. "Synthesis of New F-Alkyl β-Amino Alcohols". Synthetic Communications 21, № 6 (1991): 733–40. http://dx.doi.org/10.1080/00397919108019752.

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27

Łączkowski, Krzysztof Z., Anna Kmieciak та Anna Kozakiewicz. "Stereoselective synthesis of new monoterpene β-amino alcohols". Tetrahedron: Asymmetry 20, № 13 (2009): 1487–92. http://dx.doi.org/10.1016/j.tetasy.2009.06.007.

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28

Métro, Thomas-Xavier, Domingo Gomez Pardo та Janine Cossy. "Highly Enantioselective Synthesis of Linear β-Amino Alcohols". Chemistry - A European Journal 15, № 5 (2008): 1064–70. http://dx.doi.org/10.1002/chem.200801371.

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29

Polt, Robin, та Matt A. Peterson. "β-Amino alcohols from amino acids: Chelation control via schiff bases." Tetrahedron Letters 31, № 35 (1990): 4985–86. http://dx.doi.org/10.1016/s0040-4039(00)97784-0.

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30

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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31

Yamazaki, Shigeo, Toshifumi Takeuchi та Takenori Tanimura. "Direct enantiomeric separation of β-amino acids and β-amino alcohols by ligand-exchange chromatography". Journal of Chromatography A 540 (січень 1991): 169–75. http://dx.doi.org/10.1016/s0021-9673(01)88806-3.

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32

Bhatt, Suchitra, and Sandip K. Nayak. "Anhydrous Titanium(III) chloride as a New Lewis-Acid Catalyst for Ring Opening of Epoxides with Aromatic Amines." Natural Product Communications 2, no. 2 (2007): 1934578X0700200. http://dx.doi.org/10.1177/1934578x0700200217.

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Anhydrous titanium(III) chloride was found to be a simple and efficient Lewis acid catalyst for ring opening of epoxides at ambient temperature. The reaction proceeded smoothly with anilines as well as azide ion as nucleophiles to give the corresponding β-amino alcohols and β-azido alcohols in moderate to good yields.

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33

Narczyk, Aleksandra, Michał Pieczykolan та Sebastian Stecko. "The synthesis of non-racemic β-alkyl-β-aryl-disubstituted allyl alcohols and their transformation into allylamines and amino acids bearing a quaternary stereocenter". Organic & Biomolecular Chemistry 16, № 21 (2018): 3921–46. http://dx.doi.org/10.1039/c8ob00731d.

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34

Krishna, Chintalapudi Rama, K. Aparna Seetharam та T. N. V. S. S. Satyadev. "Synthesis of β-amino alcohols by ring opening of epoxides with amines catalyzed by sulfated tin oxide under mild and solvent-free conditions". Current Chemistry Letters 13, № 2 (2024): 343–50. http://dx.doi.org/10.5267/j.ccl.2023.11.004.

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One significant and elegant method for creating β-amino alcohols, which are useful intermediates for the synthesis of many different natural and synthetic pharmaceutical compounds, is to open the rings of epoxides with amines. When sulfated tin oxide catalyst (2 mol%) is present, epoxides can open their rings and react with amines to produce corresponding β-amino alcohols in good to high yields under mild circumstances. Under clean circumstances and in a short amount of time, the reaction demonstrated high regioselectivity and functioned well with both aromatic and aliphatic amines at room tem

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35

Nonn, Melinda, Loránd Kiss, Reijo Sillanpää та Ferenc Fülöp. "Synthesis of highly functionalized β-aminocyclopentanecarboxylate stereoisomers by reductive ring opening reaction of isoxazolines". Beilstein Journal of Organic Chemistry 8 (17 січня 2012): 100–106. http://dx.doi.org/10.3762/bjoc.8.10.

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A rapid and simple procedure was devised for the synthesis of multifunctionalized cyclic β-amino esters and γ-amino alcohols via the 1,3-dipolar cycloaddition of nitrile oxides to β-aminocyclopentenecarboxylates. The opening of the isoxazoline reductive ring to the corresponding highly functionalized 2-aminocyclopentanecarboxylates occurred stereoselectively with good yields.

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36

Leclerc, Eric, Emmanuel Vrancken та Pierre Mangeney. "Diastereoselective Aldolization of α-Aminonitriles. Diastereoselective Synthesis of β-Amino Alcohols and β,γ-Diamino Alcohols". Journal of Organic Chemistry 67, № 25 (2002): 8928–37. http://dx.doi.org/10.1021/jo025872t.

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37

Remete, Attila Márió, та Loránd Kiss. "Alicyclic β- and γ-Amino Acids: Useful Scaffolds for the Stereocontrolled Access to Amino Acid-Based Carbocyclic Nucleoside Analogs". Molecules 24, № 1 (2019): 161. http://dx.doi.org/10.3390/molecules24010161.

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Stereocontrolled synthesis of some amino acid-based carbocyclic nucleoside analogs containing ring C=C bond has been performed on β- and γ-lactam basis. Key steps were N-arylation of readily available β- or γ-lactam-derived amino ester isomers and amino alcohols with 5-amino-4,6-dichloropyrimidine; ring closure of the formed adduct with HC(OMe)3 and nucleophilic displacement of chlorine with various N-nucleophiles in the resulting 6-chloropurine moiety.

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38

Begum, Zubeda, Haruka Sannabe, Chigusa Seki та ін. "Simple primary β-amino alcohols as organocatalysts for the asymmetric Michael addition of β-keto esters to nitroalkenes". RSC Advances 11, № 1 (2021): 203–9. http://dx.doi.org/10.1039/d0ra09041g.

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39

Sergeev, Maxim E., Victor B. Pronin та Tatiana L. Voyushina. "Procedure for the Oxidation of β-Amino Alcohols to α-Amino Aldehydes". Synlett, № 18 (2005): 2802–4. http://dx.doi.org/10.1055/s-2005-918918.

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40

Siedlecka, Renata, та Jacek Skarzewski. "Synthesis of Homochiral N-Protected β-Amino Sulfoxides from α-Amino Alcohols". Synlett 1996, № 08 (1996): 757–58. http://dx.doi.org/10.1055/s-1996-5514.

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41

Kirillova, Yu G., A. V. Baranov, D. I. Prokhorov, O. V. Esipova та V. I. Shvets. "Preparative synthesis of β-amino alcohols from α-amino dicarboxylic acid derivatives". Russian Journal of Organic Chemistry 45, № 9 (2009): 1315–17. http://dx.doi.org/10.1134/s1070428009090024.

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42

MIKAMI, K., M. KANEKO, T. P. LOH, M. TERADA та T. NAKAI. "ChemInform Abstract: Amino Aldehyde-Ene Reaction: Stereoselective Route to β-Amino Alcohols." ChemInform 22, № 25 (2010): no. http://dx.doi.org/10.1002/chin.199125075.

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43

Zhang, Jian-Dong, Xiao-Xiao Yang, Qiao Jia та ін. "Asymmetric ring opening of racemic epoxides for enantioselective synthesis of (S)-β-amino alcohols by a cofactor self-sufficient cascade biocatalysis system". Catalysis Science & Technology 9, № 1 (2019): 70–74. http://dx.doi.org/10.1039/c8cy02377h.

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44

Parasuraman, Perumalsamy, Zubeda Begum, Madhu Chennapuram, et al. "Simple organocatalyst component system for asymmetric hetero Diels–Alder reaction of isatins with enones." RSC Advances 10, no. 30 (2020): 17486–91. http://dx.doi.org/10.1039/d0ra03006f.

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A simple two catalysts component system of β-amino alcohols (catalyst) and amino acids (co-catalyst) works as an efficient organocatalysts in hetero Diels–Alder reaction of isatins with enones to afford chiral spirooxindole-tetrahydropyranones.

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45

Tafelska-Kaczmarek, Agnieszka, Renata Kołodziejska, Marcin Kwit, Bartosz Stasiak, Magdalena Wypij та Patrycja Golińska. "Synthesis, Absolute Configuration, Antibacterial, and Antifungal Activities of Novel Benzofuryl β-Amino Alcohols". Materials 13, № 18 (2020): 4080. http://dx.doi.org/10.3390/ma13184080.

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A series of new benzofuryl α-azole ketones was synthesized and reduced by asymmetric transfer hydrogenation (ATH). Novel benzofuryl β-amino alcohols bearing an imidazolyl and triazolyl substituents were obtained with excellent enantioselectivity (96–99%). The absolute configuration (R) of the products was confirmed by means of electronic circular dichroism (ECD) spectroscopy supported by theoretical calculations. Selected benzofuryl α-azole ketones were also successfully asymmetrically bioreduced by fungi of Saccharomyces cerevisiae and Aureobasidium pullulans species. Racemic and chiral β-ami

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46

Wosińska-Hrydczuk, Marzena, and Jacek Skarżewski. "New Nitrogen, Sulfur-, and Selenium-Donating Ligands Derived from Chiral Pyridine Amino Alcohols. Synthesis and Catalytic Activity in Asymmetric Allylic Alkylation." Molecules 26, no. 12 (2021): 3493. http://dx.doi.org/10.3390/molecules26123493.

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Although many chiral ligands for asymmetric catalysis have been developed, there is still a need for new structures allowing the modular approach. Recently, easy synthesis of chiral pyridine-containing β-amino alcohols has been elaborated by opening respective epoxides with enantiomeric 1-phenylethylamine. This paper reports the synthetic transformation of β-amino alcohols into the new complexing pyridine-containing seleno- and thioethers. The amino alcohols were effectively converted to cyclic sulfonamidates, which were reacted with thiolates or phenyl selenide nucleophile. The reaction was d

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Lee, Michelle, Jessica R. Lamb, Maria J. Sanford, Anne M. LaPointe та Geoffrey W. Coates. "Nucleophilic ring opening of trans-2,3-disubstituted epoxides to β-amino alcohols with catalyst-controlled regioselectivity". Chemical Communications 54, № 92 (2018): 12998–3001. http://dx.doi.org/10.1039/c8cc07200k.

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Agami, Claude, Luc Dechoux та Mohand Melaimi. "An Efficient Synthesis of Pyrimidines from β-Amino Alcohols". Organic Letters 2, № 5 (2000): 633–34. http://dx.doi.org/10.1021/ol991385x.

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Fu, Xiao-Lin, та Shi-Hui Wu. "A Regio-and Stereoselective Synthesis of β-Amino Alcohols". Synthetic Communications 27, № 10 (1997): 1677–83. http://dx.doi.org/10.1080/00397919708004077.

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Andrés, JoséM, Yolanda Martín, Rafael Pedrosa та Alfonso Pérez-Encabo. "Enantioselective reformatsky reaction induced by chiral β-amino alcohols". Tetrahedron 53, № 10 (1997): 3787–94. http://dx.doi.org/10.1016/s0040-4020(97)00099-9.

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