A biocatalytic route to enantioenriched, sulfanyl aldol products

被引:15
作者
Baker-Glenn, C
Ancliff, R
Gouverneur, V
机构
[1] Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England
[2] GlaxoSmithKline, Med Res Ctr, Stevenage SG1 2NY, Herts, England
关键词
catalytic antibodies; aldol additon; sulfur;
D O I
10.1016/j.tet.2004.06.033
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The aldol products derived from sulfur- or selenium containing acceptors were prepared by kinetic resolution in the presence of antibody 84G3 with enantiomeric excesses ranging from 56 to 70%. Much higher level of enantioselectivity was obtained (enantiomeric excesses all superior to 96%) for sulfanyl aldol products derived from thiomethoxyacetone with three different acceptors. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7607 / 7619
页数:13
相关论文
共 30 条
[1]   STEREOCHEMICAL CONTROL IN THE SYNTHESIS OF TETRAHYDROFURANS BY CYCLIZATION OF DIOLS WITH PHENYLTHIO MIGRATION [J].
AGGARWAL, VK ;
COLDHAM, I ;
MCINTYRE, S ;
SANSBURY, FH ;
VILLA, MJ ;
WARREN, S .
TETRAHEDRON LETTERS, 1988, 29 (38) :4885-4888
[2]  
AGGARWAL VK, 2000, PERKIN 1, V4, P533
[3]   Immune versus natural selection: Antibody aldolases with enzymic rates but broader scope [J].
Barbas, CF ;
Heine, A ;
Zhong, GF ;
Hoffmann, T ;
Gramatikova, S ;
Bjornestedt, R ;
List, B ;
Anderson, J ;
Stura, EA ;
Wilson, IA ;
Lerner, RA .
SCIENCE, 1997, 278 (5346) :2085-2092
[4]   PHENYLSELENOACETALDEHYDE, A USEFUL REAGENT FOR THE HOMOLOGATIVE CONVERSION OF HALIDES TO PHENYLSELENOMETHYL KETONES [J].
BAUDAT, R ;
PETRZILKA, M .
HELVETICA CHIMICA ACTA, 1979, 62 (05) :1406-1410
[5]   Copying nature's mechanism for the decarboxylation of beta-keto acids into catalytic antibodies by reactive immunization [J].
Bjornestedt, R ;
Zhong, GF ;
Lerner, RA ;
Barbas, CF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (47) :11720-11724
[6]   Thermodynamically controlled cyclisation reactions with double phenylsulfanyl migration [J].
Carlisle, J ;
Fox, DJ ;
Warren, S .
CHEMICAL COMMUNICATIONS, 2003, (21) :2696-2697
[7]   Kinetic and thermodynamic control in the stereospecific synthesis of cyclic ethers via phenylsulfanyl (PhS) migration [J].
Eames, J ;
Warren, S .
TETRAHEDRON LETTERS, 1996, 37 (20) :3525-3528
[8]   Secondary and tertiary alcohols as nucleophiles in the stereospecific synthesis of substituted tetrahydrofurans by cyclisation of 1,3-diols with phenylsulfanyl migration [J].
Eames, J ;
delasHeras, MA ;
Warren, S .
TETRAHEDRON LETTERS, 1996, 37 (23) :4077-4080
[9]   Efficient alkylsulfanyl (SMe, SEt and SCH(2)Ph) and sulfanyl (SH) migration in the stereospecific synthesis of substituted tetrahydrofurans [J].
Eames, J ;
Jones, RVH ;
Warren, S .
TETRAHEDRON LETTERS, 1996, 37 (27) :4823-4826
[10]  
Fox DJ, 2002, ANGEW CHEM INT EDIT, V41, P2462, DOI 10.1002/1521-3773(20020715)41:14<2462::AID-ANIE2462>3.0.CO