Efficient 1,8- and 1,9-asymmetric inductions in the Grignard reaction of δ- and ε-keto esters of 1,1′-binaphthalen-2-ols with an oligoether tether as the 2′-substituent:: application to the synthesis of (-)-malyngolide

被引：15

作者：

Date, M

Tamai, Y

Hattori, T

Takayama, H

Kamikubo, Y

Miyano, S

机构：

[1] Tohoku Univ, Grad Sch Engn, Dept Biomol Engn, Aoba Ku, Sendai, Miyagi 9808579, Japan

[2] Nihon Univ, Coll Engn, Dept Chem & Mat Engn, Koriyama, Fukushima 9638642, Japan

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 07期

关键词：

D O I：

10.1039/b100497m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efficient 1,8- and 1,9-asymmetric inductions in the Grignard reaction of podand-type delta- (3,4) and epsilon -keto esters (5,6) are achieved in the presence of MgBr2. OEt2 with up to 97 and 82% optical yields, respectively, by using 2'-[3-(2-methoxyethoxy)propoxy]-1,1'-binaphthalen-2-ol as the chiral auxiliary. The 1,8-asymmetric inductive Grignard reaction has been advantageously utilized in the key step of a synthesis of (-)-malyngolide.

引用

页码：645 / 653

页数：9

共 23 条

[1] SYNTHESIS OF BOTH ENANTIOMERS OF OPTICALLY PURE SATURATED AND ALPHA,BETA-UNSATURATED GAMMA-SUBSTITUTED GAMMA-LACTONES FROM CHIRAL SULFOXIDES - X-RAY MOLECULAR-STRUCTURE OF (3R,4S)-4-METHYL-4-TERT-BUTYL-3-(PARA-TOLYLTHIO)BUTANOLIDE AND OF (3R,4R)-4-(CYCLOHEX-1-ENYL)-4-METHYL-3-(PARA-TOLYLTHIO)BUTANOLIDEL [J].