ENANTIOSELECTIVE CONJUGATE ADDITION .5. SYNTHESIS AND TESTING OF SCALEMIC TETRAAMINES AS CHIRAL CUPRATE LIGANDS

被引：27

作者：

SWINGLE, NM ^{[1
]}

REDDY, KV ^{[1
]}

ROSSITER, BE ^{[1
]}

机构：

[1] BRIGHAM YOUNG UNIV,DEPT CHEM & BIOCHEM,PROVO,UT 84602

来源：

TETRAHEDRON | 1994年 / 50卷 / 15期

关键词：

D O I：

10.1016/S0040-4020(01)89378-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reported herein is the enantioselective conjugate addition of n-butyl to 2-cyclopentenone, 2-cyclohexenone, 2-cycloheptenone and 2-cyclooctenone using scalemic amidocuprates derived from copper(I) iodide, n-butyllithium and a homologous series of 5 scalemic tetraamides referred to as DIMAPP-2 through -6. Cuprates derived from DIMAPP-4 manifest the highest enantioselectivities (up to 78%) and the same sense of enantioselectivity as the MAPP cuprates upon which these new cuprates are based. A previously developed mechanistic proposal has been revised to account for the observations made.

引用

页码：4455 / 4466

页数：12

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