1,3-DIPOLAR CYCLOADDITION REACTIONS OF AZOMETHINE YLIDES ON ENANTIOMERICALLY PURE (E)-GAMMA-ALKOXY-ALPHA,BETA-UNSATURATED ESTERS

被引：50

作者：

ANNUNZIATA, R

CINQUINI, M

COZZI, F

RAIMONDI, L

PILATI, T

机构：

[1] UNIV MILAN,CTR CNR,VIA CAMILLO GOLGI 19,I-20133 MILAN,ITALY

[2] UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALY

[3] CNR,CTR LO STUDIO RELAZIONI STRUTTURA & REATTIV CHIM,I-20133 MILAN,ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1991年 / 2卷 / 12期

关键词：

D O I：

10.1016/S0957-4166(00)80030-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enantiomerically pure (E)-gamma-alkoxy-alpha,beta-unsaturated esters were reacted with azomethine ylides obtained from glycine imines in the presence of LiBr and diazabicycloundecene (DBU), to afford tetrasubstituted pyrrolidines with complete regiocontrol and fair to excellent diastereoselectivity (only two diastereoisomers formed in up to 96: 4 diastereoisomeric ratio). The results are compared with those of other 1,3-dipolar cycloadditions, and the origin of stereocontrol is discussed.

引用

页码：1329 / 1342

页数：14

共 39 条

[1]

ANNUNZIATA R, 1989, GAZZ CHIM ITAL, V119, P253

[2] STEREOSELECTIVE INTRAMOLECULAR NITRONE CYCLOADDITIONS PROMOTED BY AN ALLYLIC STEREOCENTER [J].