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Journal articles on the topic 'Intramolecular aldol reaction'

Author: Grafiati

Published: 4 June 2021

Last updated: 9 February 2022

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1

Izumiseki, Atsuto, and Hisashi Yamamoto. "Intermolecular/Intramolecular Sequential Aldol Reaction." Journal of the American Chemical Society 136, no. 4 (2014): 1308–11. http://dx.doi.org/10.1021/ja413008a.

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2

Sugita, Kazuyuki, Motoi Kuwabara, Ami Matsuo, Shogo Kamo, and Akinobu Matsuzawa. "Stereoselective Convergent Synthesis of Carbon Skeleton of Cotylenin A Aglycone." Synthesis 53, no. 12 (2021): 2092–102. http://dx.doi.org/10.1055/s-0040-1706684.

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AbstractIn this paper, the synthesis of the carbon skeleton of cotylenin A aglycone is described. The key reactions, including an intramolecular aldol reaction, an aldol coupling reaction, and a ring-closing metathesis, allow for the effective and stereoselective access to the carbon skeleton of cotylenin A aglycone. The stereochemistry was confirmed by single-crystal X-ray crystallographic analyses of related compounds.

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3

Satpathi, Bishnupada, Lona Dutta, and S. S. V. Ramasastry. "Phosphine- and water-promoted pentannulative aldol reaction." Organic & Biomolecular Chemistry 17, no. 6 (2019): 1547–51. http://dx.doi.org/10.1039/c8ob03106a.

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4

Zhang, Ya-Fei, Shao-Jie Yin, Min Zhao, Jun-Qi Zhang, Hai-Yan Li, and Xing-Wang Wang. "Dinuclear zinc-catalyzed desymmetric intramolecular aldolization: an enantioselective construction of spiro[cyclohexanone-oxindole] derivatives." RSC Advances 6, no. 36 (2016): 30683–89. http://dx.doi.org/10.1039/c6ra02296k.

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A bis-ProPhenol zinc complex-catalyzed asymmetric desymmetrizing intramolecular aldol or aldol condensation reaction is reported, which furnishes spiro[cyclohexanone-oxindole] derivatives in good yields with moderate to high enantioselectivities.

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5

Banachowicz, Piotr, and Szymon Buda. "Gram-scale carbasugar synthesis via intramolecular seleno-Michael/aldol reaction." RSC Advances 9, no. 23 (2019): 12928–35. http://dx.doi.org/10.1039/c9ra02002k.

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6

Izumiseki, Atsuto, and Hisashi Yamamoto. "ChemInform Abstract: Intermolecular/Intramolecular Sequential Aldol Reaction." ChemInform 45, no. 35 (2014): no. http://dx.doi.org/10.1002/chin.201435191.

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7

Kawamoto, Yuichiro, Daiki Ozone, Toyoharu Kobayashi, and Hisanaka Ito. "Total synthesis of (±)-chondrosterin I using a desymmetric aldol reaction." Organic & Biomolecular Chemistry 16, no. 44 (2018): 8477–80. http://dx.doi.org/10.1039/c8ob02557f.

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8

Stepanova, Ekaterina, Andrey Maslivets, Svetlana Kasatkina, and Maksim Dmitriev. "Diversity-Oriented Synthesis via Catalyst-Free Addition of Ketones to [e]-Fused 1H-Pyrrole-2,3-diones." Synthesis 50, no. 24 (2018): 4897–904. http://dx.doi.org/10.1055/s-0037-1610647.

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A facile synthetic approach towards two distinct pyrrole-based heterocyclic scaffolds has been developed by the interaction of 1H-pyrrole-2,3-diones fused at the [e]-side to a 1,4-benzoxazin-2-one or quinoxalin-2(1H)-one moiety with ketones. The described interaction proceeds either as an aldol reaction or as a Michael addition/intramolecular cyclization depending on the reaction conditions. The disclosed aldol reaction proceeds with good diastereoselectivity under catalyst-free conditions when the reaction is carried out in aromatic hydrocarbons. Products of the cascade Michael addition/intra

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9

Hudlický, Miloš. "The Wichterle Reaction." Collection of Czechoslovak Chemical Communications 58, no. 10 (1993): 2229–44. http://dx.doi.org/10.1135/cccc19932229.

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The Wichterle reaction is a conversion of vinylic chlorides to ketones by sulfuric acid. Most of the applications are transformations of γ-chlorocrotyl (3-chloro-2-butenyl) derivatives to 3-oxobutyl derivatives. The ketones thus formed may undergo subsequent reactions in compounds containing reactive centers. Thus intramolecular aldol-type condensations occur in compounds containing carbonyl groups, and Friedel-Crafts-type cyclizations in compounds containing aromatic rings. The reaction can be used as an alternative to Robinson's annelation.

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10

Hagiwara, Hisahiro, Masakazu Fukushima, Kimihiko Kinugawa, Takuya Matsui, Takashi Hoshi, and Toshio Suzuki. "Total Synthesis of the Bicyclic Marine Sesquiterpenoid Drechslerine B." Natural Product Communications 6, no. 3 (2011): 1934578X1100600. http://dx.doi.org/10.1177/1934578x1100600302.

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The total synthesis of the recently isolated bicyclic sesquiterpenoid drechslerine B (2), isolated from the algicolous fungus Drechslera dematioidearare in the marine red alga Liagora viscida, has been achieved, starting from ( S)-carvone (8), via an intramolecular aldol reaction and palladium-catalyzed carbon monoxide insertion as key reactions.

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11

Liu, Song, Tao Zhang, Lei Zhu, et al. "Retro-metal-ene versus retro-Aldol: mechanistic insight into Rh-catalysed formal [3+2] cycloaddition." Chemical Communications 54, no. 96 (2018): 13551–54. http://dx.doi.org/10.1039/c8cc08335e.

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Our theoretical calculation indicated that the competition between retro-metal-ene reaction and retro-Aldol-type reaction results in the expected hexahydropentalene product together with its diastereoisomer in the newly reported rhodium-catalysed intramolecular [3+2] cycloaddition.

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12

Shing, Tony K. M., and Hau M. Cheng. "Intramolecular direct aldol reactions of sugar 2,7-diketones: syntheses of hydroxylated cycloalka(e)nones." Organic & Biomolecular Chemistry 13, no. 16 (2015): 4795–802. http://dx.doi.org/10.1039/c5ob00253b.

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A regio- and stereoselective intramolecular direct aldol reaction of 2,7-diketones derived from carbohydrates has been developed to construct cycloalkanones 7, which were dehydrated to obtain heavily oxygenated cycloalkenones 8.

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13

Sudhakar, Gangarajula, Shruthi Bayya, Vilas D. Kadam, and Jagadeesh Babu Nanubolu. "Total synthesis of gonytolides C and G, lachnone C, and formal synthesis of blennolide C and diversonol." Org. Biomol. Chem. 12, no. 30 (2014): 5601–10. http://dx.doi.org/10.1039/c4ob00950a.

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The total syntheses of gonytolide C and related compounds have been accomplished from the aldol reaction between acetophenone derived from orcinol and butyrolactone containing ketone, followed by the diastereoselective intramolecular cyclization.

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14

Yang, Lei, Shun Zhou, Jian-Qiang Zhao та ін. "A cascade deprotonation/intramolecular aldol reaction of α-carbonyl sulfonium ylides with 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes to access thieno[2,3-b]indoles and benzothiophenes". Organic & Biomolecular Chemistry 19, № 16 (2021): 3678–86. http://dx.doi.org/10.1039/d1ob00349f.

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An efficient cascade deprotonation/intramolecular aldol reaction of α-carbonyl sulfonium ylides with 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehyde was developed for the synthesis of thieno[2,3-b]indoles and benzothiophenes.

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15

Kumar, Balagani Satish, and Sadagopan Raghavan. "Stereoselective Synthesis of the A,E-Ring Bicyclic Core of Calyciphylline B-Type Alkaloids." Synlett 30, no. 19 (2019): 2157–60. http://dx.doi.org/10.1055/s-0039-1690721.

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A stereoselective synthesis of the bicyclic unit constituting the A and E rings of calyciphylline B-type alkaloids is disclosed. The propionate ester of (1R)-cyclohex-2-en-1-ol, obtained by enzymatic resolution, is subjected to an Ireland–Claisen rearrangement. Subsequent reduction of the acid, Mitsunobu reaction to introduce a nitrogen functionality, oxidative cleavage to a dialdehyde, and intramolecular aldol and aza-Michael reactions afford the bicyclic subunit.

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16

Chou, Wen-Chih, Christopher Fotsch, and Chi-Huey Wong. "Synthesis of Nitrocyclitols Based on Enzymic Aldol Reaction and Intramolecular Nitroaldol Reaction." Journal of Organic Chemistry 60, no. 9 (1995): 2916–17. http://dx.doi.org/10.1021/jo00114a051.

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17

Banachowicz, Piotr, Natalia Biduś, and Szymon Buda. "Intramolecular Tandem Seleno-Michael/Aldol Reaction—Novel Strategy in Carbasugars Synthesis." Chemistry Proceedings 2, no. 1 (2020): 25. http://dx.doi.org/10.3390/eccs2020-07571.

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Carbasugars are a wide group of carbohydrate mimetics in which the ring oxygen is replaced by a methylene group. The high importance of these compounds is related to their interesting biological and pharmacological properties which are the matter of current studies. In our work, a concise synthesis of carbasugars from naturally occurring D-pentoses is presented. The one-pot seleno-Michael reaction connected with intramolecular aldol reaction is a key step of the carbasugar core asymmetric synthesis. Further transformation of obtained carbasugar moiety led to different bioactive compounds. Tand

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18

Shiina, Isamu, Yuma Umezaki, Takatsugu Murata, Kyohei Suzuki, and Takayuki Tonoi. "Asymmetric Total Synthesis of (+)-Coprophilin." Synthesis 50, no. 06 (2017): 1301–6. http://dx.doi.org/10.1055/s-0036-1591866.

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In this paper, we report the first total synthesis of (+)-coprophilin, an anticoccidial agent, by constructing the chiral linear precursor via a Mukaiyama–Evans aldol reaction and a stereoselective intramolecular Diels–Alder reaction. The proposed method can be used to provide large amounts of (+)-coprophilin, which exhibits a 3,4,5,6,7-pentasubstituted Δ1,2-octalin core structure.

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19

Fu, Shaomin, Bo Liu, Yongjiang Liu, Yanhui Zhang, and Xiao Wang. "Synthesis of Polycyclic Frameworks through Iron-Catalyzed Intramolecular [5+2] Cycloaddition." Synlett 29, no. 15 (2018): 1978–82. http://dx.doi.org/10.1055/s-0037-1610258.

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A concise and efficient approach to the core of the C18/C19 diterpenoid alkaloids and phomopsterone B is reported. Both syntheses share the same iron-catalyzed intramolecular [5+2] cycloaddition to assemble the tricyclo[6.3.1.01,6]]dodecane skeleton. The following approach to the 6/5/6/7 tetracyclic core scaffold of C18/C19 diterpenoid alkaloids features a regioselective Grignard addition/thermal Claisen rearrangement/RCM cyclization. Meanwhile the synthetic steps to access the spiro 6/5/6 tricyclic subunits of phomopsterone B were characterized as intramolecular aldol reaction, Wacker oxidat

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20

Tanino, Keiji, and Hideomi Yamaga. "Synthesis of Substituted Cyclopentenol Derivatives via Intramolecular Addition Reaction of Vinylcopper Species." Synlett 30, no. 02 (2018): 230–34. http://dx.doi.org/10.1055/s-0037-1611366.

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A new method for the synthesis of substituted cyclopentenes is developed, based on an intramolecular 1,2-addition reaction of vinylcopper species generated from 1,1-dibromoalkene derivatives. The substrates are prepared from ketones through the aldol reaction with 3,3-dibromoacrolein followed by silylation of the hydroxyl group. Treatment of the substrate with excess Me2CuLi results in the formation of 3-methyl-2-cyclopenten-1-ol derivatives with good yields.

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21

Miesch, Laurence, Vincent Rietsch, Tania Welsch, and Michel Miesch. "Intramolecular alkynylogous Mukaiyama aldol type reaction mediated by TBSOTf/NEt3." Tetrahedron Letters 49, no. 34 (2008): 5053–55. http://dx.doi.org/10.1016/j.tetlet.2008.06.038.

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22

Renard, Pierre-Yves, and Jean-Yves Lallemand. "A Construction of PolyoxygenatedcisandtransDecalin Systems by an Intramolecular Aldol Reaction." Synlett 1993, no. 02 (1993): 163–64. http://dx.doi.org/10.1055/s-1993-22389.

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23

Wang, Pu-Sheng, Kang-Nan Li, Xiao-Le Zhou, et al. "Enantioselective Relay Catalytic Cascade Intramolecular Hydrosiloxylation and Mukaiyama Aldol Reaction." Chemistry - A European Journal 19, no. 20 (2013): 6234–38. http://dx.doi.org/10.1002/chem.201300702.

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24

Stockman, Robert A., Peter Szeto, Stephen H. J. Thompson, Michael S. Hadley, David C. Lathbury, and Timothy Gallagher. "Synthesis of Functionalised Azabicycles via a Regiospecific Intramolecular Aldol Reaction." Synlett 1996, no. 09 (1996): 853–55. http://dx.doi.org/10.1055/s-1996-5598.

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25

David Rodriguez, Fredy A., Mauricio Maldonado Villamil, and James Guevara-Pulido. "Organocatalytic Cascade Reaction of Aliphatic Enals and Benzoylnitromethane: Synthesis of Enantioenriched Tetrasubstituted Cyclohexene Carbaldehyde." Journal of Chemistry 2020 (June 28, 2020): 1–9. http://dx.doi.org/10.1155/2020/9248793.

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A new example of the reactivity of enals with benzoylnitromethane was studied in a Michael-Michael-Aldol-Dehydration quadruple organocascade reaction. The reaction unexpectedly yielded a tetrasubstituted cyclohexene carbaldehyde with excellent enantiomeric excess when crotonaldehyde was used as the Michael-acceptor, whereas using (E)-Hex-2-enal as the Michael-acceptor formed a cyclic hemiacetal by steering the reaction into the intramolecular formation of the same intermediate via a Michael-Heterocyclization domino reaction.

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26

Enders, Dieter, Jeanne Fronert, Tom Bisschops, and Florian Boeck. "Asymmetric total synthesis of smyrindiol employing an organocatalytic aldol key step." Beilstein Journal of Organic Chemistry 8 (July 18, 2012): 1112–17. http://dx.doi.org/10.3762/bjoc.8.123.

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The first organocatalytic asymmetric synthesis of smyrindiol, by using an (S)-proline catalyzed enantioselective intramolecular aldol reaction as the key step, is described. Smyrindiol was synthesized from commercially available 2,4-dihydroxybenzaldehyde in 15 steps, with excellent stereoselectivity (de = 99%, ee = 99%). In the course of this total synthesis a new and mild coumarin assembly was developed.

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27

Ishida, Hiroaki, Shinya Kimura, Noriyuki Kogure, Mariko Kitajima, and Hiromitsu Takayama. "The first asymmetric total synthesis of lycoposerramine-R." Organic & Biomolecular Chemistry 13, no. 28 (2015): 7762–71. http://dx.doi.org/10.1039/c5ob00827a.

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The first asymmetric total synthesis of lycoposerramine-R was accomplished by a strategy featuring the stereoselective intramolecular aldol cyclization giving a cis-fused 5/6 bicyclic skeleton and a new method for the construction of the pyridone ring via the aza-Wittig reaction, thereby establishing the absolute configuration of the natural product.

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28

Ihara, Masataka, Takahiko Taniguchi, Masami Yamada, Yuji Tokunaga, and Keiichiro Fukumoto. "Stereocontrolled intramolecular michael-aldol reaction mediated with bu2botf and (tms)2nh." Tetrahedron Letters 36, no. 44 (1995): 8071–74. http://dx.doi.org/10.1016/0040-4039(95)01711-p.

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29

CHOU, W. C., C. FOTSCH, and C. H. WONG. "ChemInform Abstract: Synthesis of Nitrocyclitols Based on Enzymatic Aldol Reaction and Intramolecular Nitroaldol Reaction." ChemInform 26, no. 37 (2010): no. http://dx.doi.org/10.1002/chin.199537245.

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30

Stöckl, Yannick, Wolfgang Frey, Johannes Lang, Birgit Claasen, Angelika Baro, and Sabine Laschat. "Asymmetric Organocatalysis Revisited: Taming Hydrindanes with Jørgensen–Hayashi Catalyst." Synthesis 51, no. 05 (2018): 1123–34. http://dx.doi.org/10.1055/s-0037-1610409.

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The organocatalytic Michael reaction of easily available 1-cyclopentene-1-carbaldehyde and 1,3-dicarbonyl compounds led to cyclopentanecarbaldehydes on a gram scale with low catalyst loading (2 mol%) and high enantioselectivity. The synthetic potential of 4-acylhexahydroindenones from intramolecular aldol condensation was demonstrated by Diels–Alder reaction to a tetracyclic derivative with seven stereogenic centers. The diastereofacial preference of the tetracyclic product was confirmed by DFT calculations. The described reaction sequence is characterized by few redox-economic steps and high

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31

Beck, Ellen J., Bruce Twitchin, and Lewis N. Mander. "Radio labelling of the gibberellin plant growth inhibitor 16,17-dihydro-GA5." Canadian Journal of Chemistry 82, no. 2 (2004): 293–300. http://dx.doi.org/10.1139/v03-202.

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An improved five-step procedure has been developed for the synthesis of the gibberellin plant growth inhibitor 16,17-dihydro-GA5 from gibberellic acid. The 3-13C and 3-14C derivatives of this material have also been prepared by excising C-3 from the carbon skeleton (ozonolysis of a Δ2-alkene derivative and subsequent retro-Claisen reaction) and then reassembling the A-ring by means of an intramolecular aldol reaction.Key words: gibberellin, growth inhibitor, degradation, Radio labelling, Wittig reaction.

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32

Nakamura, Eiichi, Go Sakata, and Katsumi Kubota. "The olefinic aldol reaction. Intramolecular cyclization forming five- and six-membered rings." Tetrahedron Letters 39, no. 15 (1998): 2157–58. http://dx.doi.org/10.1016/s0040-4039(98)00145-2.

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33

Freirı́a, Marta, Andrew J. Whitehead, Derek A. Tocher, and William B. Motherwell. "Further observations on the rhodium (I)-catalysed tandem hydrosilylation-intramolecular aldol reaction." Tetrahedron 60, no. 11 (2004): 2673–92. http://dx.doi.org/10.1016/j.tet.2003.12.057.

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34

Shigehisa, Hiroki, Takashi Mizutani, Shin-ya Tosaki, Takashi Ohshima, and Masakatsu Shibasaki. "Formal total synthesis of (+)-wortmannin using catalytic asymmetric intramolecular aldol condensation reaction." Tetrahedron 61, no. 21 (2005): 5057–65. http://dx.doi.org/10.1016/j.tet.2005.03.038.

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35

Kobayashi, Toyoharu, Hideki Abe, and Hisanaka Ito. "Synthetic Studies of Polycyclic Terpenoids Using the Intramolecular Aldol-Type Cyclization Reaction." Journal of Synthetic Organic Chemistry, Japan 77, no. 11 (2019): 1086–95. http://dx.doi.org/10.5059/yukigoseikyokaishi.77.1086.

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36

Hashigaki, Kuniko, Sabroh Yoshioka, and Masatoshi Yamato. "Synthesis of Carbocyclic Spiro Compounds from Isochroman Derivatives via Intramolecular Aldol Reaction." Synthesis 1986, no. 12 (1986): 1004–7. http://dx.doi.org/10.1055/s-1986-31849.

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37

Hammar, Peter, Cynthia Ghobril, Cyril Antheaume, Alain Wagner, Rachid Baati, and Fahmi Himo. "Theoretical Mechanistic Study of the TBD-Catalyzed Intramolecular Aldol Reaction of Ketoaldehydes." Journal of Organic Chemistry 75, no. 14 (2010): 4728–36. http://dx.doi.org/10.1021/jo100488g.

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38

STOCKMAN, R. A., P. SZETO, S. H. J. THOMPSON, M. S. HADLEY, D. C. LATHBURY, and T. GALLAGHER. "ChemInform Abstract: Synthesis of Functionalized Azabicycles via a Regiospecific Intramolecular Aldol Reaction." ChemInform 28, no. 8 (2010): no. http://dx.doi.org/10.1002/chin.199708121.

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39

Gazaille, Jeffrey A., Joseph A. Abramite, and Tarek Sammakia. "Toward the Synthesis of (+)-Peloruside A via an Intramolecular Vinylogous Aldol Reaction." Organic Letters 14, no. 1 (2011): 178–81. http://dx.doi.org/10.1021/ol202966m.

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40

Wang, Pu-Sheng, Kang-Nan Li, Xiao-Le Zhou, et al. "ChemInform Abstract: Enantioselective Relay Catalytic Cascade Intramolecular Hydrosiloxylation and Mukaiyama Aldol Reaction." ChemInform 44, no. 40 (2013): no. http://dx.doi.org/10.1002/chin.201340196.

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41

Sakakura, Akira, Kai Onda та Ichiro Hayakawa. "Reinvestigation of the Biomimetic Cyclization of 3,5-Diketo Esters: Application to the Total Synthesis of Cyercene A, an α-Methoxy-γ-Pyrone-Containing Polypropionate". Synlett 28, № 13 (2017): 1596–600. http://dx.doi.org/10.1055/s-0036-1588795.

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The biomimetic cyclization of 3,5-diketo esters was reinvestigated for the synthesis of α-methoxy-γ-pyrones. 3,5-Diketo esters were selectively synthesized via the aldol reaction of commercially available methyl 2-methyl-3-oxopentanoate with an aldehyde followed by the oxidation with AZADOL® and PhI(OAc)2. The DBU-promoted intramolecular transesterification of 3,5-diketo esters showed excellent reactivity in MeOH, to give the corresponding γ-hydroxy-α-pyrones in high yields under mild reaction conditions. Based on the present cyclization scheme, the total synthesis of cyercene A was achieved.

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42

Lu, Jianyu, Serkan Koldas, Huafang Fan, John Desper, Victor W. Day, and Duy H. Hua. "A One-Pot Intramolecular Tandem Michael–Aldol Annulation Reaction for the Synthesis of Chiral Pentacyclic Terpenes." Synthesis 51, no. 21 (2019): 3964–72. http://dx.doi.org/10.1055/s-0039-1690521.

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A chiral tricyclic terpene possessing a 6,6,6-tricyclic framework and a 3,3-dimethyl-7-oxooctylidenyl side chain undergoes a double ring-closing reaction to give two chiral pentacyclic terpenes in a ratio of 4:3 via an intramolecular Michael addition followed by aldol condensation under basic conditions. Three new stereogenic centers are introduced in the initial Michael annulation reaction. Stereoselective installation of an ethoxycarbonyl group at C17 of the two pentacyclic terpenes separately gives the corresponding highly functionalized pentacyclic terpenoids with seven stereogenic centers

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43

Suzuki, Takahiro, Riko Nagahama, Muhammad Aiman Fariz, Yuki Yukutake, Kazutada Ikeuchi, and Keiji Tanino. "Synthesis of Illisimonin a Skeleton by Intramolecular Diels–Alder Reaction of Ortho-Benzoquinones and Biomimetic Skeletal Rearrangement of Allo-Cedranes." Organics 2, no. 3 (2021): 306–12. http://dx.doi.org/10.3390/org2030016.

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Illisimonin A is a new sesquiterpene isolated from Illicium simonsii, and it possesses a novel 5/5/5/5/5 pentacyclic skeleton. The tricyclic skeleton of illisimonin A, tricyclo[5.2.1.01,5]decane, is presumed to be biosynthesized from allo-cedranes via a skeletal rearrangement. Herein, we report the concise synthesis of highly oxidized allo-cedranes by an intramolecular Diels–Alder reaction using ortho-benzoquinones and demonstrate the biomimetic transformation of allo-cedranes by a retro-Claisen/aldol pathway.

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44

Meanwell, Michael, Steven M. Silverman, Johannes Lehmann, et al. "A short de novo synthesis of nucleoside analogs." Science 369, no. 6504 (2020): 725–30. http://dx.doi.org/10.1126/science.abb3231.

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Nucleoside analogs are commonly used in the treatment of cancer and viral infections. Their syntheses benefit from decades of research but are often protracted, unamenable to diversification, and reliant on a limited pool of chiral carbohydrate starting materials. We present a process for rapidly constructing nucleoside analogs from simple achiral materials. Using only proline catalysis, heteroaryl-substituted acetaldehydes are fluorinated and then directly engaged in enantioselective aldol reactions in a one-pot reaction. A subsequent intramolecular fluoride displacement reaction provides a f

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45

Yeung, Chi-Tung, Wesley Chan, Wai-Sum Lo, Ga-Lai Law, and Wing-Tak Wong. "Synthesis of a Conformationally Stable Atropisomeric Pair of Biphenyl Scaffold Containing Additional Stereogenic Centers." Molecules 24, no. 3 (2019): 643. http://dx.doi.org/10.3390/molecules24030643.

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The synthesis of a new CF3-containing stereogenic atropisomeric pair of ortho-disubstituted biphenyl scaffold is presented. The atropisomers are surprisingly conformationally stable for isolation. X-ray structures show that their stability comes from an intramolecular hydrogen bond formation from their two hydroxyl groups and renders the spatial arrangement of their peripheral CF3 and CH3 groups very different. The synthesized stereogenic scaffold proved to be effective in catalyzing the asymmetric N-nitroso aldol reaction of enamine and nitrosobenzene. Compared to similar scaffolds without CF

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46

Wang, Cunde, Xushun Qing, Ting Wang, Chenlu Dai, and Zhenjie Su. "Direct Synthesis of 6H-Chromeno[3,4-b]quinolin-6-ol Derivatives from Substituted 3-Nitro-2H-chromenes and 2-Nitrobenzaldehydes Mediated by Fe/AcOH System." Synthesis 50, no. 06 (2017): 1350–58. http://dx.doi.org/10.1055/s-0036-1589154.

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An efficient iron/acetic acid system-mediated reductive cyclization reaction of substituted 2-aryl-3-nitro-2H-chromenes with substituted 2-nitrobenzaldehydes for the synthesis of 6-aryl-6H-chromeno[3,4-b]quinolines was developed. This reaction involves the sequential reduction, hydrolysis, aldol condensation, intramolecular addition, and the nucleophilic addition of substituted 2-aryl-3-nitro-2H-chromenes with substituted 2-nitrobenzaldehydes to give the corresponding 6H-chromeno[3,4-b]quinolines. This transformation provides a straightforward synthetic protocol for constructing substituted 6H

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47

Banert, Klaus, Manuel Heck, Andreas Ihle, Erik Michael, and Richard Weber. "Record-Breaking Steric Crowding in Trialkylamines Prepared by Oxidative Ring Opening." Synthesis 52, no. 24 (2020): 3801–10. http://dx.doi.org/10.1055/s-0040-1707294.

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AbstractEpoxidation of olefinic heterocyclic amines and subsequent acid-catalyzed hydrolysis or alternatively the direct dihydroxylation with the help of osmium tetroxide led to diols, which underwent ring cleavage in the presence of lead tetraacetate to give 3-isopropyl-2,2,4,4-tetramethyl-3-azahexanedial and 3-tert-butyl-2,2,4,4-tetramethyl-3-azapentanedial. Whereas the former dialdehyde is a highly unstable model compound because of a rapid intramolecular aldol reaction, the latter product proves to be isolable at room temperature. Furthermore, this compound is the first open-chain tri-tert

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48

Abramite, Joseph A., and Tarek Sammakia. "Application of the Intramolecular Yamamoto Vinylogous Aldol Reaction to the Synthesis of Macrolides." Organic Letters 9, no. 11 (2007): 2103–6. http://dx.doi.org/10.1021/ol0704901.

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IHARA, M., T. TANIGUCHI, M. YAMADA, Y. TOKUNAGA, and K. FUKUMOTO. "ChemInform Abstract: Stereocontrolled Intramolecular Michael-Aldol Reaction Mediated with Bu2BOTf and (TMS)2NH." ChemInform 27, no. 7 (2010): no. http://dx.doi.org/10.1002/chin.199607101.

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Yang, Heng, Dandan Liu, Qinqin Yu, et al. "DBU-Promoted Intramolecular Crossed Aldol Reaction: A Facile Access to Indane-Fused Pyrrolidine." European Journal of Organic Chemistry 2019, no. 4 (2018): 852–56. http://dx.doi.org/10.1002/ejoc.201801513.

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