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.
引用
收藏
页码：2706 / 2709
页数：4
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