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
[51]   Synthesis of (S)-α-tocotrienol via an enzymatic desymmetrization of an achiral chroman derivative [J].
Chênevert, R ;
Courchesne, G .
TETRAHEDRON LETTERS, 2002, 43 (44) :7971-7973
[52]   Chemoenzymatic synthesis of both enantiomers of cis-6-(hydroxymethyl)- and cis,cis-4-hydroxy-6-(hydroxymethyl)pipecolic acids [J].
Chênevert, R ;
Morin, MP .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) :3178-3180
[53]   Enzymatic desymmetrization of a meso polyol corresponding to the C(19)-C(27) segment of rifamycin S [J].
Chênevert, R ;
Rose, YS .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (06) :1707-1709
[54]   Chemoenzymatic enantioselective synthesis of (-)-indolizidine 167 B [J].
Chênevert, R ;
Ziarani, GM ;
Dasser, M .
HETEROCYCLES, 1999, 51 (03) :593-598
[55]   Enzymatic route to chiral, nonracemic cis-2,6- and cis,cis-2,4,6-substituted piperidines. Synthesis of (+)-dihydropinidine and dendrobate alkaloid (+)-241D [J].
Chenevert, R ;
Dickman, M .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3332-3341
[56]   The anomalous course of the microsomal transformation of the exo-2,3-epoxides of norbornene and norbornadiene.: The possible involvement of a general acid activation during the enzymatic hydrolysis of these oxides [J].
Chiappe, C ;
De Rubertis, A ;
Marioni, F ;
Simonetti, A .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2000, 10 (05) :539-544
[57]   Highly efficient extractive biocatalysis in the asymmetric reduction of an acyclic enone by the yeast Pichia stipitis [J].
Conceiçao, GJA ;
Moran, PJS ;
Rodrigues, JAR .
TETRAHEDRON-ASYMMETRY, 2003, 14 (01) :43-45
[58]  
Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO
[59]  
2-V
[60]  
Crosby J., 1997, CHIRALITY IND