ENANTIOSELECTIVE PROTONATION OF ACHIRAL LITHIUM ENOLATES USING A CHIRAL AMINE IN THE PRESENCE OF LITHIUM BROMIDE

被引：80

作者：

YASUKATA, T ^{[1
]}

KOGA, K ^{[1
]}

机构：

[1] UNIV TOKYO,FAC PHARMACEUT SCI,BUNKYO KU,TOKYO 113,JAPAN

来源：

TETRAHEDRON-ASYMMETRY | 1993年 / 4卷 / 01期

关键词：

D O I：

10.1016/S0957-4166(00)86011-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Asymmetric synthesis of 2-alkyl-1-tetralones (2) was achieved in up to 91 % e.e. by enantioselective protonation of their corresponding achiral lithium enolates (4) using a chiral amine ((R)-l) as a chiral source in the presence of lithium bromide. Enantioselective alkylation using (R)-1 was also carried out, and it is found that the alkyl halide prefers the si-face of the lithium enolate 6 as oppose to the re-face preference of 4a in case of protonation.

引用

页码：35 / 38

页数：4

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