A practical synthesis of C2-symmetric chiral binaphthyl ketone catalyst

被引：4

作者：

Seki, M ^{[1
]}

Yamada, S ^{[1
]}

Kuroda, T ^{[1
]}

Imashiro, R ^{[1
]}

Shimizu, T ^{[1
]}

机构：

[1] Tanabe Seiyaku Co Ltd, Prod & Technol Dev Lab, Yodogawa Ku, Osaka 5328505, Japan

来源：

SYNTHESIS-STUTTGART | 2000年 / 12期

关键词：

catalysts; asymmetric epoxidation; dioxiranes; macrocycles; optical resolution;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical synthesis of 11-membered C-2-symmetric binaphthyl ketone (R)-1, a catalyst for asymmetric epoxidation, was developed. (+/-)-1,1'-Binaphthyl-2,2'-dicarboxylic acid [(+/-)-6] was efficiently resolved by (R)-(-)-1-cyclohexylethylamine to give (R)-6 in >99% ee and in 38% yield. Condensation of the acid chloride derived from (R)-6 with 1,3-dihydroxyacetone dimer at 60-70 degreesC provided the desired chiral ketone (R)-1 in 61-63% yield without need for high dilution techniques.

引用

页码：1677 / 1680

页数：4

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