ASYMMETRIC-SYNTHESIS OF AXIALLY CHIRAL 1,1'-BIPHENYL-2-CARBOXYLATES VIA NUCLEOPHILIC AROMATIC-SUBSTITUTION ON 2-MENTHOXYBENZOATES BY ARYL GRIGNARD-REAGENTS

被引：28

作者：

HATTORI, T ^{[1
]}

KOIKE, N ^{[1
]}

MIYANO, S ^{[1
]}

机构：

[1] TOHOKU UNIV,FAC ENGN,DEPT BIOCHEM & ENGN,AOBA KU,SENDAI,MIYAGI 980,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 16期

关键词：

D O I：

10.1039/p19940002273

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical method is presented for an asymmetric synthesis of axially chiral 1,1'-biphenyl-2-carboxylates via the ester-assisted nucleophilic aromatic substitution reaction. Thus, upon treatment of 2-tert-butylphenyl 2-[(-)-menthoxy]benzoates with an aryl Grignard reagent, chirality of the leaving (-)-menthoxy group is transferred to the newly formed biphenyl linkage with up to 94% optical yield.

引用

收藏

页码：2273 / 2282

页数：10

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