NUCLEOPHILIC AROMATIC-SUBSTITUTION ON 1-ALKOXY-2-NAPHTHOATES WITH 1-NAPHTHYL GRIGNARD-REAGENTS - A PRACTICAL AND CONVENIENT ASYMMETRIC-SYNTHESIS OF 1,1'-BINAPHTHYL-2-CARBOXYLATES

被引：74

作者：

HATTORI, T ^{[1
]}

HOTTA, H ^{[1
]}

SUZUKI, T ^{[1
]}

MIYANO, S ^{[1
]}

机构：

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

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1993年 / 66卷 / 02期

关键词：

D O I：

10.1246/bcsj.66.613

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

1-Naphthyl Grignard reagents efficiently displace the I-alkoxyl group of I-alkoxy-2-naphthoic esters to provide an easy access to the corresponding 1,1'-binaphthyl-2-carboxylates in excellent yields: isopropyl ester is bulky enough to prevent the Grignard addition to the ester carbonyl function. High levels of asymmetric induction (up to 98% optical yield) have been achieved in the joining of the two naphthalene rings by using 1-(l-p-menth-3-yloxy)-2-naphthoates, while the reaction of chiral alkyl esters of 1-methoxy-2-naphthoic acid proceeded with appreciable to moderate stereoselectivity. The probable reaction mechanisms are discussed for the binaphthyl coupling and the asymmetric induction.

引用

页码：613 / 622

页数：10

共 37 条

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[2] Optical activity and the polarity of substituent groups. Part IX. Menthyl esters of methoxynaphthoic and of diphenyl-2-carboxylic acids. [J].