Synthesis of the first enantiomerically pure 3-thiazolines via Asinger reaction

被引:26
作者
Schlemminger, I [1 ]
Janknecht, HH [1 ]
Maison, W [1 ]
Saak, W [1 ]
Martens, J [1 ]
机构
[1] Carl von Ossietzky Univ Oldenburg, Dept Chem, D-26111 Oldenburg, Germany
关键词
Asinger reaction; imines; thiazolines; enantioselection;
D O I
10.1016/S0040-4039(00)01266-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first synthesis of an enantiomerically and diastereomerically pure 3-thiazoline via modified Asinger reaction using a galactose derived chiral auxiliary is described. The absolute configuration of this heterocyclic imine has been elucidated via X-ray analysis. In addition, the 3-thiazoline has been successfully derivatized under Ugi conditions. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7289 / 7292
页数:4
相关论文
共 17 条
[2]  
ASINGER F, 1956, ANGEW CHEM INT EDIT, V68, P377
[3]   NOVEL STEREOCHEMICAL MANIPULATIONS OF THE PENICILLIN NUCLEUS [J].
BALDWIN, JE ;
CHAN, RY ;
SUTHERLAND, JD .
TETRAHEDRON LETTERS, 1994, 35 (30) :5519-5522
[4]  
DRAUZ K, 1985, LIEBIGS ANN CHEM, P448
[5]  
Groger H, 1996, Z NATURFORSCH B, V51, P1305
[6]   Synthesis of glutathione analogues, peptide nucleic acids and phosphonooligopeptides from heterocyclic imines [J].
Groger, H ;
Hatam, M ;
Kintscher, J ;
Martens, J .
SYNTHETIC COMMUNICATIONS, 1996, 26 (18) :3383-3394
[7]   1,2-3,4-DI-O-ISOPROPYLIDENE-ALPHA-D-GALACTO-HEXODIALDO-1,5-PYRANOSE AND ITS 6-ALDEYDROL [J].
HORTON, D ;
NAKADATE, M ;
TRONCHET, JM .
CARBOHYDRATE RESEARCH, 1968, 7 (01) :56-&
[8]   SYNTHESIS OF SACCHARIDES AND RELATED POLYHYDROXYLATED NATURAL-PRODUCTS .1. SIMPLE ALDITOLS [J].
KATSUKI, T ;
LEE, AWM ;
MA, P ;
MARTIN, VS ;
MASAMUNE, S ;
SHARPLESS, KB ;
TUDDENHAM, D ;
WALKER, FJ .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (07) :1373-1378
[9]  
Maison W, 1999, EUR J ORG CHEM, V1999, P2433
[10]   FACILE SYNTHESIS OF RACEMIC CYSTEINE [J].
MARTENS, J ;
OFFERMANNS, H ;
SCHERBERICH, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1981, 20 (08) :668-668