Highly (E)-Selective BF3•Et2O-Promoted Allylboration of Chiral Nonracemic α-Substituted Allylboronates and Analysis of the Origin of Stereocontrol

被引：48

作者：

Chen, Ming ^{[1
]}

Roush, William R. ^{[1
]}

机构：

[1] Scripps Florida, Dept Chem, Jupiter, FL 33458 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 12期

基金：

美国国家卫生研究院;

关键词：

ALLYL-TRANSFER REACTION; CATALYTIC ENANTIOSELECTIVE ALLYLBORATION; STEREOSELECTIVE TOTAL SYNTHESIS; C-BOND FORMATION; HOMOALLYLIC ALCOHOLS; LEWIS-ACID; ASYMMETRIC-SYNTHESIS; PRINS-CYCLIZATION; LINEAR SYNTHESIS; EFFICIENT ROUTE;

D O I：

10.1021/ol1007444

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

delta-Methyl-substituted homoallylic alcohols 2 were prepared in 71-88% yield, E:Z>30:1 and 93% to >95% ee via BF3 center dot Et2O-promoted allylboration with alpha-Me-allylboronate 1. The origin of high (E)-selectivity is proposed.

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页码：2706 / 2709

页数：4

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