B-2'-ISOPRENYLDIISOPINOCAMPHEYLBORANE - AN EFFICIENT REAGENT FOR THE CHIRAL ISOPRENYLATION OF ALDEHYDES - A CONVENIENT ROUTE TO BOTH ENANTIOMERS OF IPSENOL AND IPSDIENOL

被引:25
作者
BROWN, HC
RANDAD, RS
机构
[1] H. C. Brown and R. B. Wetherill Laboratories of Chemistry, Purdue University, West Lafayette
关键词
D O I
10.1016/0040-4039(90)87006-L
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
B-2′-Isoprenyldiisopinocampheylborane is prepared by metallation of isoprene with potassium 2,2,5,5-tetramethylpiperidide followed by sequential treatment with B-methoxydiisopinocampheylborane and boron trifluoride-etherate. Condensation of this reagent with aldehydes provides isoprenylated chiral alcohols. This methodology is utilized for an efficient one-pot synthesis of both enantiomers of the pheromones of the bark beetle Ips paraconfusus Lanier, ipsenol and ipsdienol in 96% ee and 65% isolated yields. © 1990.
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页码:455 / 458
页数:4
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