SYNTHESIS OF S-TRIFLUOROMETHYL-CONTAINING ALPHA-AMINO-ACIDS FROM SODIUM TRIFLUOROMETHANESULFINATE AND DITHIO-AMINO ACIDS

被引:56
作者
LANGLOIS, B
MONTEGRE, D
ROIDOT, N
机构
[1] Université Claude Bernard-Lyon I, Laboratoire de Chimie Organique 3, associé au CNRS, F-69622 Villeurbanne Cedex, 43 Bd. du
关键词
D O I
10.1016/0022-1139(93)02982-K
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
N-Protonated or N-acetylated dimethyl cystinates and homocystinates react with sodium trifluoromethanesulfinate and t-butyl hydroperoxide to yield the corresponding derivatives of methyl S-trifluoromethyl cysteinate and homocysteinate in a stereospecific manner. Methyl S-trifluoromethyl-N-acetyl cysteinate and homocysteinate are readily saponified, without racemization, by sodium hydrogen carbonate in a water/methanol mixture.
引用
收藏
页码:63 / 66
页数:4
相关论文
共 15 条
[1]  
Boiko V.N., 1979, ZH ORG KHIM, V14, P396
[2]  
BOIKO VN, 1977, ZH ORG KHIM+, V13, P1057
[3]   PERFLUOROALKYLATION OF 2-MERCAPTOBENZOTHIAZOLE AND ITS ANALOGS WITH PERFLUOROALKYL IODIDES BY AN SRN1 REACTION [J].
CHEN, QY ;
CHEN, MJ .
JOURNAL OF FLUORINE CHEMISTRY, 1991, 51 (01) :21-32
[4]  
Clavel J. - L., 1991, PHOSPHORUS SULFUR, V59, P169, DOI DOI 10.1080/10426509108045716
[5]   PERFLUOROALKYLATION OF THIOLS - EVIDENCE FOR A RADICAL CHAIN PROCESS [J].
FEIRING, AE .
JOURNAL OF FLUORINE CHEMISTRY, 1984, 24 (02) :191-203
[6]  
GANDELSMAN LZ, 1977, UKR KHIM ZH+, V43, P1224
[8]   FACILE SYNTHESIS OF FLUORINATED METHIONINES [J].
HOUSTON, ME ;
HONEK, JF .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (12) :761-762
[9]   PERFLUOROALKYLATION OF THIOLS BY PEFLUOROALKYLBROMIDES [J].
IGNATEV, NV ;
BOIKO, VN ;
YAGUPOLSKII, LM .
JOURNAL OF FLUORINE CHEMISTRY, 1985, 29 (1-2) :210-210
[10]   CLEAVAGE OF ESTERS USING CARBONATES AND BICARBONATES OF ALKALI-METALS - SYNTHESIS OF THYMOPENTIN [J].
KAESTLE, KL ;
ANWER, MK ;
AUDHYA, TK ;
GOLDSTEIN, G .
TETRAHEDRON LETTERS, 1991, 32 (03) :327-330