Efficient and selective synthesis of (S,R,R,S,R,S)-4,6,8,10,16,18-hexamethyl-docosane via Zr-catalyzed asymmetric carboalumination of alkenes (ZACA reaction)

被引：39

作者：

Zhu, Gangguo ^{[1
]}

Liang, Bo ^{[1
]}

Negishi, Ei-ichi ^{[1
]}

机构：

[1] Purdue Univ, Herbert C Brown Labs Chem, W Lafayette, IN 47907 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 06期

关键词：

D O I：

10.1021/ol703056u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(S,R,R,S,R,S)-4,6,8,10,16,18-Hexamethyldocosane (1) was synthesized in 11% yield in 11 steps in the longest linear sequence from >= 98% pure (S)-beta-citronellal and 6 additional steps for the preparation of 11 in 23% yield from propene. Five of the six asymmetric carbon centers were generated catalytically and stereoselectively by the ZACA reaction (5 times), one lipase-catalyzed acetylation, and two chromatographic operations.

引用

页码：1099 / 1101

页数：3

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