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Journal articles on the topic 'Diastereoselective reduction'

Author: Grafiati

Published: 4 June 2021

Last updated: 5 February 2022

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1

Pereira, Vera L. P., Francine P. Meirelis та Bruna G. N. Vieira. "Divergent and Diastereoselective Synthesis of α-Monosubstituted and trans-α,β-Disubstituted γ-Lactams from (S)-N,N-Dibenzyl-α-amino Aldehydes via Henry and Michael Reactions". Synthesis 52, № 23 (2020): 3650–56. http://dx.doi.org/10.1055/s-0040-1706423.

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γ-Monosubstituted and trans-α,β-disubstituted γ-lactams were diastereoselectively synthesized from common intermediates (S)-N,N-dibenzylated aldehydes derived from natural l-(α)-amino acids, employing a divergent approach. The key features of the routes include diastereoselective Henry and Michael reactions that produced chiral γ-nitroester derivatives, which were subsequently submitted to a tandem reduction-lactamization sequence providing the title compounds. The versatility of routes can allow the preparation of several other mono-, di-, or tri-substituted γ-lactams.

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2

Ramaswamy, Sowmianarayanan, and Allan C. Oehlschlager. "Efficient synthesis of exo- and endo-brevicomin from a single precursor." Canadian Journal of Chemistry 67, no. 5 (1989): 794–96. http://dx.doi.org/10.1139/v89-120.

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Diastereoselective reduction of 2-propionyl-6-methyl-3,4-dihydropyran and its ring opened derivatives, followed by acidic work-up, gives mixtures rich (>9:1) of either exo- or endo-brevicomin. Keywords: exo- and endo-brevicomin, diastereoselective ketone reduction.

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3

Zielinski, Claudia, and Hans J. Schäfer. "Diastereoselective cathodic reduction of chiral phenylglyoxylamides." Tetrahedron Letters 35, no. 31 (1994): 5621–24. http://dx.doi.org/10.1016/s0040-4039(00)77263-7.

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4

Tavtorkin, A. N., L. A. Sviridova, G. A. Golubeva, Yu V. Nelyubina, K. A. Lyssenko та K. A. Kochetkov. "Diastereoselective reduction of α-pyrazolidinyl ketones". Russian Chemical Bulletin 58, № 3 (2009): 624–30. http://dx.doi.org/10.1007/s11172-009-0066-7.

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5

Lóránda, Tamás, Erzsébet Osza, Gyula Kispála, et al. "Diastereoselective reduction of cyclic bioactive Mannich ketones." Arkivoc 2004, no. 7 (2003): 34–52. http://dx.doi.org/10.3998/ark.5550190.0005.704.

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6

Malamakal, Roy M., Whitney R. Hess та Todd A. Davis. "Highly Efficient Diastereoselective Reduction of α-Fluoroimines". Organic Letters 12, № 10 (2010): 2186–89. http://dx.doi.org/10.1021/ol100647b.

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7

Mohanta, Pramod K., Todd A. Davis, Jeremy R. Gooch та Robert A. Flowers. "Chelation-Controlled Diastereoselective Reduction of α-Fluoroketones". Journal of the American Chemical Society 127, № 34 (2005): 11896–97. http://dx.doi.org/10.1021/ja052546x.

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8

Miyashita, Kazuyuki, Tomohiro Toyoda, Hideto Miyabe та Takeshi Imanishi. "Diastereoselective Reduction of α-(p-Tolylsulfinyl)ketoximes". Synlett 1995, № 12 (1995): 1229–31. http://dx.doi.org/10.1055/s-1995-5253.

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9

Salom-Roig, Xavier, and Claude Bauder. "Recent Applications in the Use of Sulfoxides as Chiral Auxiliaries for the Asymmetric Synthesis of Natural and Biologically Active Products." Synthesis 52, no. 07 (2020): 964–78. http://dx.doi.org/10.1055/s-0039-1690803.

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The contribution of chiral sulfoxides as versatile auxiliaries in the field of organic chemistry has shown a prevalent interest in the asymmetric synthesis of natural products during the last 45 years. In this short review, we report the recent applications of these chiral auxiliaries to the synthesis of natural and biological active products highlighted from 2010 to 2019. We hope to allow the reader to have an overview of the potential of sulfoxide chemistry in the field of enantioselective synthesis.1 Introduction2 Diastereoselective Additions to Ketones2.1 Reduction of β-Keto Sulfoxides2.2

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10

Chen, Kau-Ming, Goetz E. Hardtmann, Kapa Prasad, Oljan Repič та Michael J. Shapiro. "1,3- diastereoselective reduction of β-hydroxyketones utilizing alkoxydialkylboranes". Tetrahedron Letters 28, № 2 (1987): 155–58. http://dx.doi.org/10.1016/s0040-4039(00)95673-9.

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11

Byun, Il Suk, та Yong Hae Kim. "Highly Diastereoselective Reduction of New Chiral α-Ketoamides". Synthetic Communications 25, № 13 (1995): 1963–69. http://dx.doi.org/10.1080/00397919508015873.

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12

Aswathanarayanappa, C., E. Bheemappa, and Yadav D. Bodke. "Diastereoselective Reduction of the Enone Intermediate of Travoprost." Organic Process Research & Development 15, no. 5 (2011): 1085–87. http://dx.doi.org/10.1021/op200154p.

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13

Schäfer, A., and B. Schäfer. "Diastereoselective protonation after the Birch reduction of pyrroles." Tetrahedron 55, no. 42 (1999): 12309–12. http://dx.doi.org/10.1016/s0040-4020(99)00730-9.

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14

Nakamura, Kaoru, Yasushi Kawai, Takehiko Miyai, and Atsuyoshi Ohno. "Stereochemical control in diastereoselective reduction with baker's yeast." Tetrahedron Letters 31, no. 25 (1990): 3631–32. http://dx.doi.org/10.1016/s0040-4039(00)94462-9.

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15

Tavtorkin, A. N., L. A. Sviridova, G. A. Golubeva, Yu V. Nelyubina, K. A. Lyssenko та K. A. Kochetkov. "ChemInform Abstract: Diastereoselective Reduction of α-Pyrazolidinyl Ketones." ChemInform 41, № 35 (2010): no. http://dx.doi.org/10.1002/chin.201035123.

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16

Kim, Bong Chan, and Won Koo Lee. "Highly diastereoselective reduction of enantiomerically pure aziridino ketones." Tetrahedron 52, no. 37 (1996): 12117–24. http://dx.doi.org/10.1016/0040-4020(96)00703-x.

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17

Clavier, John W., Joseph Fievet, and Victoria Geisler. "NMR Verification of Diastereoselective Reduction of Substituted Cyclohexanones." Chemical Educator 5, no. 2 (2000): 64–66. http://dx.doi.org/10.1007/s00897990366a.

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18

O’Neil, Gregory, and Trevor Stockdale. "Regio- and Diastereoselective Samarium-Mediated Allylic Benzoate Reductions." Synlett 28, no. 17 (2017): 2267–71. http://dx.doi.org/10.1055/s-0036-1590831.

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A regio- and diastereoselective samarium(II)-mediated reduction of allylic benzoates is described. Yields for the reactions are generally high with diastereoselectivities up to 90:10 and in some cases only a single regioisomer was obtained. The stereoselectivity of the reaction is proposed to arise from chelation of a hydroxyl-stereocenter and starting alkene geometry, with protonation occurring intramolecularly by samarium-bound water.

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19

Lhommet, Gérard, Giang Vo Thanh, Jean-Pierre Célérier, Anne Fleurant, Cyrille Grandjean, and Sylvie Rosset. "Diastereoselective Reduction of Cyclic Imines and b-Enamino Esters." HETEROCYCLES 43, no. 7 (1996): 1381. http://dx.doi.org/10.3987/com-96-7479.

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20

Li, Li-Ping, He-Long Peng, Lian-Qiang Wei, and Bao-Hui Ye. "Diastereoselective Photooxidation and Reduction of Chiral Iridium(III) Complexes." Inorganic Chemistry 58, no. 1 (2018): 785–93. http://dx.doi.org/10.1021/acs.inorgchem.8b02934.

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21

McLaughlin, Noel, Colm Duffy, Francesco Alletto та ін. "Diastereoselective sulfonate-directed carbonyl reduction of γ-keto-sulfonates". Tetrahedron Letters 60, № 19 (2019): 1313–16. http://dx.doi.org/10.1016/j.tetlet.2019.03.065.

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22

Pilli, R. A., D. Russowsky та L. C. Dias. "Diastereoselective reduction of acyclic N-aryl-β-amino ketones". J. Chem. Soc., Perkin Trans. 1, № 4 (1990): 1213–14. http://dx.doi.org/10.1039/p19900001213.

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23

Sarko, Christopher R., Ian C. Guch, and Marcello DiMare. "Chelation-controlled protocol for the diastereoselective reduction of ketones." Journal of Organic Chemistry 59, no. 4 (1994): 705–6. http://dx.doi.org/10.1021/jo00083a004.

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24

Gualandi, A., and D. Savoia. "Substrate induced diastereoselective hydrogenation/reduction of arenes and heteroarenes." RSC Advances 6, no. 22 (2016): 18419–51. http://dx.doi.org/10.1039/c5ra23908g.

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25

Asano, Keisuke, Seijiro Matsubara та Akira Matsumoto. "Diastereoselective Reduction of β-(1,3-Dioxan-4-yl)ketones". Synlett 26, № 13 (2015): 1872–74. http://dx.doi.org/10.1055/s-0034-1378725.

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26

Zohar, Elinor, and Ilan Marek. "Diastereoselective Reduction of Cyclopropenylcarbinol: New Access toanti-Cyclopropylcarbinol Derivatives." Organic Letters 6, no. 3 (2004): 341–43. http://dx.doi.org/10.1021/ol036143i.

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27

Khan, Faiz Ahmed, Jyotirmayee Dash та Ch Sudheer. "Indium-Mediated Regio- and Diastereoselective Reduction of Norbornylα-Diketones". Chemistry - A European Journal 10, № 10 (2004): 2507–19. http://dx.doi.org/10.1002/chem.200305656.

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28

MIYASHITA, K., T. TOYODA, H. MIYABE та T. IMANISHI. "ChemInform Abstract: Diastereoselective Reduction of α-(p-Tolylsulfinyl)ketoximes." ChemInform 27, № 16 (2010): no. http://dx.doi.org/10.1002/chin.199616097.

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29

Malamakal, Roy M., Whitney R. Hess та Todd A. Davis. "ChemInform Abstract: Highly Efficient Diastereoselective Reduction of α-Fluoroimines." ChemInform 41, № 40 (2010): no. http://dx.doi.org/10.1002/chin.201040038.

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30

Grossert, J. Stuart, H. Ranjith W. Dharmaratne, T. Stanley Cameron та Beverly R. Vincent. "Steric effects in the diastereoselective reduction of β-ketosulfones". Canadian Journal of Chemistry 66, № 11 (1988): 2860–69. http://dx.doi.org/10.1139/v88-443.

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The stereochemical course of the reduction of ketones adjacent to a chiral center normally shows some diastereoselectivity (described by Cram's rule), the degree of which is dependent on the structure of the ketone and on the reaction conditions; the selectivity in acyclic species is often not very great. In this paper, we describe the sodium borohydride reduction of four acyclic β-ketosulfones, containing a chiral center at the α position, in which the products are formed with high diastereoselectivity. Reasons for this selectivity became apparent when we were able to show that these ketosulf

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31

Fraser, David S., Sheldon B. Park та J. Michael Chong. "Diastereoselective reduction of α-aminoketones: Synthesis of anti- and syn-β-aminoalcohols". Canadian Journal of Chemistry 82, № 2 (2004): 87–101. http://dx.doi.org/10.1139/v03-165.

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Reduction of N-t-BOC-protected-N-alkyl α-aminoketones with LiEt3BH or Li(s-Bu)3BH furnishes protected syn-β-aminoalcohols with high selectivities. In contrast, removal of the BOC group followed by reduction of the aminoketone gives anti-β-aminoalcohols with variable selectivities. With aromatic ketones, selectivities are typically high while aliphatic ketones show mediocre to high selectivities depending on steric considerations.Key words: β-aminoalcohol, diastereoselective reduction.

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32

Asaoka, Morio, Masami Satoh, Sakurako Washida, and Sawako Takeuchi. "Highly Diastereoselective Reduction of g-Keto Amides: Diastereoselective Synthesis of g-Butyrolactones with Contiguous Chiral Centers." HETEROCYCLES 52, no. 1 (2000): 227. http://dx.doi.org/10.3987/com-99-s14.

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33

Audin, Patrick, Catherine Pothion, Jean-Alain Fehrentz, Andre Loffet, Jean Martinez та Joëlle Paris. "Diastereoselective Synthesis of N-Protected β-Amino-α-hydroxyacids (Norstatines) from Urethane N-Carboxyanhydrides (UNCAs)". Journal of Chemical Research 23, № 4 (1999): 282–83. http://dx.doi.org/10.1177/174751989902300418.

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β-Amino-α-hydroxyacids (norstatines) are prepared from urethane N-protected carboxyanhydrides (UNCAs); the key step is the diastereoselective reduction of a keto-acetylenic compound, which lead is, with syn diastereoselectivity, to the corresponding propargylic alcohol.

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34

Shimizu, Makoto, Yasuki Niwa, Takeshi Nagai та Iwao Hachiya. "Diastereoselective Reduction of α-Imino Esters with Tris(trimethylsilyl)aluminum". HETEROCYCLES 72, № 1 (2007): 127. http://dx.doi.org/10.3987/com-06-s(k)23.

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35

Calvet, Sandrine, Olivier David, Corinne Vanucci-Bacqué, Marie-Claude Fargeau-Bellassoued та Gérard Lhommet. "Chiral heterocyclic β-enamino esters: convenient synthesis and diastereoselective reduction". Tetrahedron 59, № 33 (2003): 6333–39. http://dx.doi.org/10.1016/s0040-4020(03)00980-3.

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36

Quinto, Tommaso, Daniel Häussinger, Valentin Köhler, and Thomas R. Ward. "Artificial metalloenzymes for the diastereoselective reduction of NAD+ to NAD2H." Organic & Biomolecular Chemistry 13, no. 2 (2015): 357–60. http://dx.doi.org/10.1039/c4ob02071e.

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37

Stankevič, Marek. "Diastereoselective desymmetrization of diarylphosphinous acid-borane amides under Birch reduction." Organic & Biomolecular Chemistry 13, no. 21 (2015): 6082–102. http://dx.doi.org/10.1039/c4ob02440k.

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38

Schaefer, A., and B. Schaefer. "ChemInform Abstract: Diastereoselective Protonation after the Birch Reduction of Pyrroles." ChemInform 31, no. 3 (2010): no. http://dx.doi.org/10.1002/chin.200003117.

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39

KIM, B. C., and W. K. LEE. "ChemInform Abstract: Highly Diastereoselective Reduction of Enantiomerically Pure Aziridino Ketones." ChemInform 28, no. 5 (2010): no. http://dx.doi.org/10.1002/chin.199705055.

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40

BYUN, I. S., та Y. H. KIM. "ChemInform Abstract: Highly Diastereoselective Reduction of New Chiral α-Ketoamides." ChemInform 26, № 38 (2010): no. http://dx.doi.org/10.1002/chin.199538086.

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41

Fioravanti, Stefania, Federico Mancinelli, Luca Parise, Alessia Pelagalli, Lucio Pellacani та Laura Trulli. "β,β-Dialkyl γ-amino γ-trifluoromethyl alcohols from trifluoromethyl (E)-aldimines by a one-pot solvent-free Mannich-type reaction and subsequent reduction". RSC Advances 6, № 104 (2016): 101862–68. http://dx.doi.org/10.1039/c6ra22507a.

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A diastereoselective one-pot solvent-free Mannich-type addition of α-alkyl aldehydes to trifluoromethyl (E)-aldimines, which first act as bases and then as electrophiles, leads to β,β-dialkyl γ-amino γ-CF<sub>3</sub> alcohols in good yields, after reduction.

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42

Satoh, Masami, Sakurako Washida, Sawako Takeuchi та Morio Asaoka. "ChemInform Abstract: Highly Diastereoselective Reduction of γ-Keto Amides: Diastereoselective Synthesis of γ-Butyrolactones with Contiguous Chiral Centers." ChemInform 31, № 14 (2010): no. http://dx.doi.org/10.1002/chin.200014088.

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43

Bunce, Richard A., Derrick M. Herron, Lara B. Johnson, and Sharadsrikar V. Kotturi. "Diastereoselective Synthesis of Substituted Tetrahydroquinoline-4-carboxylic Esters by a Tandem Reduction−Reductive Amination Reaction." Journal of Organic Chemistry 66, no. 8 (2001): 2822–27. http://dx.doi.org/10.1021/jo001761n.

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44

Bunce, Richard A., Derrick M. Herron, Jason R. Lewis, Sharadsrikar V. Kotturi, and Elizabeth M. Holt. "Diastereoselective synthesis of linear-fused tricyclic nitrogen heterocycles by a tandem reduction-reductive amination reaction." Journal of Heterocyclic Chemistry 40, no. 1 (2003): 101–6. http://dx.doi.org/10.1002/jhet.5570400113.

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45

Wei, Pei-Hsun, Melanie A. Gary, Divya Nalla та ін. "Diastereoselective formation of β-hydroxyketones by the reduction of Ketene dimers". Tetrahedron Letters 54, № 8 (2013): 932–35. http://dx.doi.org/10.1016/j.tetlet.2012.12.011.

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46

Sharov, Victor S., Deborah A. Ferrington, Thomas C. Squier, and Christian Schöneich. "Diastereoselective reduction of protein-bound methionine sulfoxide by methionine sulfoxide reductase." FEBS Letters 455, no. 3 (1999): 247–50. http://dx.doi.org/10.1016/s0014-5793(99)00888-1.

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47

Buisson, Didier, and Robert Azerad. "Diastereoselective and enantioselective microbial reduction of cyclic alpha-alkyl beta-ketoesters." Tetrahedron Letters 27, no. 23 (1986): 2631–34. http://dx.doi.org/10.1016/s0040-4039(00)84603-1.

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48

B. MacLean, David, Zbigniew Czarnocki, and Walter A. Szarek. "Diastereoselective Reduction of Derivatives of 3,4-Dihydro-1-methylidene-2-tartaroylisoquinoline." HETEROCYCLES 34, no. 5 (1992): 943. http://dx.doi.org/10.3987/com-91-5959.

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49

Murphy, Rebecca A., Anthony Y. Chen, Sajiv K. Nair, Gary M. Gallego, Neal W. Sach, and Graham Smith. "Diastereoselective access to substituted 4-aminopiperidines via a pyridine reduction approach." Tetrahedron Letters 57, no. 50 (2016): 5588–91. http://dx.doi.org/10.1016/j.tetlet.2016.10.107.

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50

Shirahata, Makoto, Hiroshi Yamazaki, and Shin-ichi Fukuzawa. "Highly Diastereoselective Reduction of Chiral (Ferrocenylseleno)methyl Aryl and Alkyl Ketones." Chemistry Letters 28, no. 3 (1999): 245–46. http://dx.doi.org/10.1246/cl.1999.245.

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