A SIMPLE ASYMMETRIC-SYNTHESIS OF 2-SUBSTITUTED PYRROLIDINES FROM 3-ACYLPROPIONIC ACIDS

被引:85
作者
MEYERS, AI
BURGESS, LE
机构
[1] Department of Chemistry, Colorado State University, Fort Collins
关键词
D O I
10.1021/jo00007a011
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The title compounds have been prepared from 3-acylpropionic acids 2 and (-)-R-phenylglycinol in a three-step sequence in > 98% enantiomeric excess. The R group in 2 ultimately becomes the 2-substituent in the chiral pyrrolidine.
引用
收藏
页码:2294 / 2296
页数:3
相关论文
共 28 条
[1]   CHIRAL ACETALS IN ASYMMETRIC-SYNTHESIS [J].
ALEXAKIS, A ;
MANGENEY, P .
TETRAHEDRON-ASYMMETRY, 1990, 1 (08) :477-511
[2]   ASYMMETRIC-SYNTHESIS .13. SYNTHESIS OF 2-ALKYLPYRROLIDINES - TOWARDS AZABICYCLIC SYSTEMS [J].
ARSENIYADIS, S ;
HUANG, PQ ;
HUSSON, HP .
TETRAHEDRON LETTERS, 1988, 29 (06) :631-634
[3]   ASYMMETRIC MICHAEL ADDITIONS - STEREOSELECTIVE ALKYLATIONS OF THE (R)-ENAMINE AND (S)-ENAMINE FROM CYCLOHEXANONE AND 2-(METHOXYMETHYL)PYRROLIDINE BY METHYL ALPHA-(METHOXYCARBONYL)CINNAMATES [J].
BLARER, SJ ;
SEEBACH, D .
CHEMISCHE BERICHTE-RECUEIL, 1983, 116 (06) :2250-2260
[5]   FURTHER SYNTHETIC STUDIES ON THE CONVERSION OF ALCOHOLS INTO PHENYLTHIO ETHERS [J].
CLEARY, DG .
SYNTHETIC COMMUNICATIONS, 1989, 19 (5-6) :737-744
[6]   MECHANISTIC AND STEREOCHEMICAL DIVERGENCE IN THE ALLYLSILANE-ACETAL ADDITION-REACTION [J].
DENMARK, SE ;
WILLSON, TM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (09) :3475-3476
[7]  
DEPEREZ RMB, 1986, J ORG CHEM, V51, P2039
[8]   ALKYLLITHIUM REAGENTS FROM ALKYL-HALIDES AND LITHIUM RADICAL-ANIONS [J].
FREEMAN, PK ;
HUTCHINSON, LL .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (10) :1924-1930
[9]   STEREOCHEMISTRY OF THE REACTIONS OF LITHIUM DI-TERT-BUTYLBIPHENYL WITH ALKYL-HALIDES [J].
FREEMAN, PK ;
HUTCHINSON, LL .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (24) :4705-4713
[10]  
GANEM B, 1990, SYNLETT, P503