SYNTHESIS OF BETA,GAMMA-UNSATURATED D-ALPHA-AMINO ACIDS FROM L-CYSTEINE

被引:27
作者
DUTHALER, RO
机构
[1] Central Research Laboratories, Ciba-Geigy Ag, Basel, CH-4002, Post Office Box
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1991年 / 30卷 / 06期
关键词
D O I
10.1002/anie.199107051
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
D-alpha-Amino-acids 2 are accessible in high optical purity by acid hydrolysis of the 5-thiazolidinone 1. Compounds of the type 1 can be prepared in a few reaction steps from L-cysteine; during the conversion of 1 into 2 unsaturated residues R remain intact. Boc = tert-butoxycarbonyl.
引用
收藏
页码:705 / 707
页数:3
相关论文
共 52 条
[41]   A NEW NUCLEOPHILIC ALANINOL SYNTHON FROM SERINE [J].
SIBI, MP ;
RENHOWE, PA .
TETRAHEDRON LETTERS, 1990, 31 (51) :7407-7410
[42]  
SUFRIN JR, 1982, BIOCHEM BIOPH RES CO, V106, P251, DOI 10.1016/0006-291X(82)91102-0
[43]   ALPHA-HYDROPEROXY SULFIDE IN SULFIDE PHOTOOXIDATION - FORMATION AND ISOLATION IN THE PHOTOOXIDATION OF THIAZOLIDINE DERIVATIVES IN APROTIC MEDIA [J].
TAKATA, T ;
HOSHINO, K ;
TAKEUCHI, E ;
TAMURA, Y ;
ANDO, W .
TETRAHEDRON LETTERS, 1984, 25 (42) :4767-4770
[44]   NEW SYNTHETIC UTILITY OF SINGLET OXYGEN IN SULFIDE PHOTO-OXIDATION - SELECTIVE AND STEREOSPECIFIC HYDROXYLATION-ALPHA TO SULFUR OF 4-SUBSTITUTED "3-BENZOYL-2,2-DIMETHYLTHIAZOLIDINES [J].
TAKATA, T ;
TAMURA, Y ;
ANDO, W .
TETRAHEDRON, 1985, 41 (11) :2133-2137
[45]   SYNTHESIS AND REACTIONS OF CYCLIC ALPHA-HYDROXY SULFIDES [J].
TAKATA, T ;
HUANG, L ;
ANDO, W .
CHEMISTRY LETTERS, 1985, (11) :1705-1708
[46]   SILICON PUMMERER REACTION OF THIAZOLIDINE S-OXIDES - A NEW METHOD FOR STEREOSPECIFIC C-5 FUNCTIONALIZATION OF THIAZOLIDINES [J].
TOKITOH, N ;
IGARASHI, Y ;
ANDO, W .
TETRAHEDRON LETTERS, 1987, 28 (47) :5903-5906
[47]   SUICIDE SUBSTRATES - MECHANISM-BASED ENZYME INACTIVATORS [J].
WALSH, C .
TETRAHEDRON, 1982, 38 (07) :871-909
[48]   METHIONINE AS PRECURSOR FOR THE ENANTIOSELECTIVE SYNTHESIS OF ALPHA-BRANCHED VINYLGLYCINES AND OF OTHER AMINO-ACIDS [J].
WEBER, T ;
AESCHIMANN, R ;
MAETZKE, T ;
SEEBACH, D .
HELVETICA CHIMICA ACTA, 1986, 69 (06) :1365-1377
[49]  
Williams R.M., 1989, ORGANIC CHEM SERIES, V1
[50]  
WILLIAMS RM, 1988, TETRAHEDRON, V44, P5425