ENANTIOSELECTIVE CONJUGATE ADDITION TO CYCLIC ENONES WITH SCALEMIC LITHIUM ORGANO(AMIDO)CUPRATES .4. RELATIONSHIP BETWEEN LIGAND STRUCTURE AND ENANTIOSELECTIVITY

被引：78

作者：

ROSSITER, BE

EGUCHI, M

MIAO, G

SWINGLE, NM

HERNANDEZ, AE

VICKERS, D

FLUCKIGER, E

PATTERSON, RG

REDDY, KV

机构：

[1] Department of Chemistry, Brigham Young University, Provo

来源：

TETRAHEDRON | 1993年 / 49卷 / 05期

关键词：

D O I：

10.1016/S0040-4020(01)86278-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Scalemic lithium amides derived from primary and secondary amines react with organocopper compounds in ether or dimethyl sulfide to form lithium organo(amido)cuprates capable of enantioselective conjugate addition to 2-cycloalkenones. The most successful heterocuprate, in which the chiral ligand is (S)-N-methyl-1-phenyl-2-(1-piperidinyl)ethanamine, (S)-MAPP, 13, reacts with cyclic enones to form products with up to 97% ee. Non-linear asymmetric induction was observed with the cuprate formed from ligand 13.

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页码：965 / 986

页数：22

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