METAL-ION CATALYZED ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION REACTIONS OF IMINES OF ALPHA-AMINO ESTERS

被引：60

作者：

BARR, DA

DORRITY, MJ

GRIGG, R

MALONE, JF

MONTGOMERY, J

RAJVIROONGIT, S

STEVENSON, P

机构：

[1] UNIV LEEDS,SCH CHEM,LEEDS LS2 9JT,W YORKSHIRE,ENGLAND

[2] MAHIDOL UNIV,DEPT CHEM,BANGKOK 10700,THAILAND

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 45期

关键词：

D O I：

10.1016/S0040-4039(00)97119-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cycloaddition of a range of imines of α-amino esters to homochiral menthyl acrylate proceeds with complete asymmetric induction at room temperature in the presence of silver(I), lithium(I) and thallium(I) salts. The imine of 2-aminomethylpyridine reacts similarly. Reversal of cycloaddition regiochemistry, together with complete asymmetric induction, occurs when titanium (IV) complexes are used as catalysts. The absolute configuration of one of the cycloadducts has been established by X-ray crystallography. © 1990.

引用

页码：6569 / 6572

页数：4

共 5 条

[1] X=Y-ZH COMPOUNDS AS POTENTIAL 1,3-DIPOLES .24. PREPARATION AND THERMAL FRAGMENTATION OF IMIDAZOLIDINES - INFLUENCE OF METAL-SALTS ON PYRROLIDINE VERSUS IMIDAZOLIDINE FORMATION [J].