Enantioselective construction of bicyclo[3.1.0]hexane derivatives through asymmetric deprotonation of meso-cyclic ketones

被引：4

作者：

Abe, H ^{[1
]}

Tsujino, T ^{[1
]}

Araki, K ^{[1
]}

Takeuchi, Y ^{[1
]}

Harayama, T ^{[1
]}

机构：

[1] Okayama Univ, Fac Pharmaceut Sci, Okayama 7008530, Japan

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 14期

关键词：

D O I：

10.1016/S0957-4166(02)00405-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

An efficient asymmetric synthesis of bicyclo[3.1.0]hexane derivatives was achieved. The three-step conversion of 6-hydroxytricyclo[3.2.1.0(2,7)]octan-3-one 2, (derived from 3-oxatricyclo[3.3.1.0(2,4)]nonan-7-one 1 through an asymmetric deprotonation reaction) led to 6 in optically active form. Alternatively, the asymmetric deprotonation reaction of meso-cyclic ketones 9a and 9b with several chiral lithium amide bases was examined to give silyl enol ether 12 and triflate 21 with high enantioselectivity. The absolute configuration of the triflate 21 was determined by investigation of the chemical relationship between 21 and 6. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1519 / 1527

页数：9

共 14 条

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