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
收藏
页码：1099 / 1101
页数：3
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