Viable use of 2-substituted thiazolidine-4-methanol diastereoisomeric mixtures during asymmetric borane reduction of aromatic ketones

被引:24
作者
Calmes, M [1 ]
Escale, F [1 ]
Paolini, F [1 ]
机构
[1] UNIV MONTPELLIER 2,UMR CNRS 5810,LAB AMINOACIDES PEPTIDES & PROT,F-34095 MONTPELLIER 5,FRANCE
关键词
D O I
10.1016/S0957-4166(97)00480-1
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The reduction of aromatic ketones by borane in the presence of the inseparable diastereoisomeric mixture of 2-substituted thiazolidine-4-methanol has been investigated. Modest to high enantiomeric excesses were obtained increasing with thiazolidine steric hindrance. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:3691 / 3697
页数:7
相关论文
共 28 条
[1]   CATALYTIC ASYMMETRIC HYDROBORATION WITH OXAZABOROLIDINES [J].
BROWN, JM ;
LLOYDJONES, GC .
TETRAHEDRON-ASYMMETRY, 1990, 1 (12) :869-872
[2]   REDUCTION OF ESTERS WITH SODIUM BOROHYDRIDE [J].
BROWN, MS ;
RAPOPORT, H .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (11) :3261-&
[3]   ASYMMETRIC SYNTHESES .20. ENANTIOSELECTIVE HYDROSILYLATION OF KETONES WITH [RH(COD)CL]2 THIAZOLIDINE CATALYSTS [J].
BRUNNER, H ;
BECKER, R ;
RIEPL, G .
ORGANOMETALLICS, 1984, 3 (09) :1354-1359
[4]   STEREOSPECIFIC TOTAL SYNTHESIS OF D-BIOTIN FROM L(+)-CYSTEINE [J].
CONFALONE, PN ;
PIZZOLATO, G ;
BAGGIOLINI, EG ;
LOLLAR, D ;
USKOKOVIC, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (21) :7020-7026
[5]   HIGHLY ENANTIOSELECTIVE ALKYNYLATION OF ALDEHYDES PROMOTED BY CHIRAL OXAZABOROLIDINES [J].
COREY, EJ ;
CIMPRICH, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :3151-3152
[6]   HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].
COREY, EJ ;
BAKSHI, RK ;
SHIBATA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553
[7]   NOVEL ELECTRONIC EFFECTS OF REMOTE SUBSTITUENTS ON THE OXAZABOROLIDINE-CATALYZED ENANTIOSELECTIVE REDUCTION OF KETONES [J].
COREY, EJ ;
HELAL, CJ .
TETRAHEDRON LETTERS, 1995, 36 (50) :9153-9156
[8]   ASYMMETRIC BORON-CATALYZED REACTIONS [J].
DELOUX, L ;
SREBNIK, M .
CHEMICAL REVIEWS, 1993, 93 (02) :763-784
[9]   PROTECTED DERIVATIVES OF (R)-CYSTEINE AND (R)-CYSTEINOL [J].
GONZALEZ, A ;
LAVILLA, R ;
PINIELLA, JF ;
ALVAREZLARENA, A .
TETRAHEDRON, 1995, 51 (10) :3015-3024
[10]   SYNTHESIS AND STRUCTURE OF 2-SUBSTITUTED DERIVATIVES OF 4-ETHYL(R) THIAZOLIDINE CARBOXYLATE [J].
HAMRI, A ;
PERA, MH ;
FILLION, H .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1987, 24 (06) :1629-1633