Enantioselective enzymatic desymmetrizations in organic synthesis

被引:442
作者
García-Urdiales, E
Alfonso, I
Gotor, V
机构
[1] Univ Oviedo, Fac Quim, Dept Quim Organ & Inorgan, E-33071 Oviedo, Spain
[2] Univ Jaume 1, Dept Quim Organ & Inorgan, Castellon de La Plana 12071, Spain
关键词
D O I
10.1021/cr040640a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Enantioselective enzymatic desymmetrizations (EEDs) of meso and prochiral substrates have proved to be a powerful methodology that allows the preparation of a wide range of optically active building blocks in a highly enantioselective fashion and in high yields. Furthermore in most cases, enantiodivergence can be achieved by means of the employment of different enzymes, substrate engineering, or combination with other approaches such as kinetic resolutions (KRs) or metal catalysis. These factors make EEDs an attractive tool of asymmetric synthesis and convert them into an active field of research.
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页码:313 / 354
页数:42
相关论文
共 299 条
[1]   α hydroxylation of carboxylic acids with molecular oxygen catalyzed by the α oxidase of peas (Pisum sativum):: A novel biocatalytic synthesis of enantiomerically pure (R)-2-hydroxy acids [J].
Adam, W ;
Boland, W ;
Hartmann-Schreier, J ;
Humpf, HU ;
Lazarus, M ;
Saffert, A ;
Saha-Moller, CR ;
Schreier, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (43) :11044-11048
[2]   A highly enantioselective biocatalytic sulfoxidation by the topsoil bacterium Pseudomonas frederiksbergensis [J].
Adam, W ;
Heckel, F ;
Saha-Möller, CR ;
Taupp, M ;
Schreier, P .
TETRAHEDRON-ASYMMETRY, 2004, 15 (06) :983-985
[3]  
Adam W, 2000, EUR J ORG CHEM, V2000, P2923, DOI 10.1002/1099-0690(200008)2000:16<2923::AID-EJOC2923>3.0.CO
[4]  
2-L
[5]   Biocatalytic asymmetric hydroxylation of hydrocarbons by free and immobilized Bacillus megaterium cells [J].
Adam, W ;
Lukacs, Z ;
Kahle, C ;
Saha-Möller, CR ;
Schreier, P .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2001, 11 (4-6) :377-385
[6]   Biocatalytic asymmetric hydroxylation of hydrocarbons with the topsoil-microorganism Bacillus megaterium [J].
Adam, W ;
Lukacs, Z ;
Harmsen, D ;
Saha-Möller, CR ;
Schreier, P .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (03) :878-882
[7]   Enantiodivergent preparation of optically active oxindoles having a stereogenic quaternary carbon center at the C3 position via the lipase-catalyzed desymmetrization protocol: Effective use of 2-furoates for either enzymatic esterification or hydrolysis [J].
Akai, S ;
Tsujino, T ;
Akiyama, E ;
Tanimoto, K ;
Naka, T ;
Kita, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (07) :2478-2486
[8]   Efficient lipase-catalyzed enantioselective desymmetrization of prochiral 2,2-disubstituted 1,3-propanediols and meso 1,2-diols using 1-ethoxyvinyl 2-furoate [J].
Akai, S ;
Naka, T ;
Fujita, T ;
Takeba, Y ;
Tsujino, T ;
Kita, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (02) :411-419
[9]   1-Ethoxyvinyl 2-furoate, an efficient acyl donor for the lipase-catalyzed enantioselective desymmetrization of prochiral 2,2-disubstituted propane-1,3-diols and meso-1,2-diols [J].
Akai, S ;
Naka, T ;
Fujita, T ;
Takebe, Y ;
Kita, Y .
CHEMICAL COMMUNICATIONS, 2000, (16) :1461-1462
[10]   Lipase-catalyzed enantioselective desymmetrization of prochiral 3,3-bis(hydroxymethyl)oxindoles [J].
Akai, S ;
Tsujino, T ;
Naka, T ;
Tanimoto, K ;
Kita, Y .
TETRAHEDRON LETTERS, 2001, 42 (41) :7315-7317