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.
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页码：2273 / 2282
页数：10
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