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

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 04期

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.

引用

页码：455 / 458

页数：4

共 32 条

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