Indium-Promoted Chemo- and Diastereoselective Allylation of α,β-Epoxy Ketones with Potassium Allyltrifluoroborate

被引：26
|
作者：
Nowrouzi, Farhad [1 ]
Janetzko, John [1 ]
Batey, Robert A. [1 ]
机构：
[1] Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 23期
基金：
加拿大自然科学与工程研究理事会;
关键词：
CATALYTIC ASYMMETRIC ALLYLATION; ANTI CROTYLATION; EPOXY ALCOHOLS; AQUEOUS-MEDIA; ALDEHYDES; ALLYLBORATION; EPOXIDES; ALPHA; TRIFLUOROBORATE; ALLYLINDIUM;
D O I：
10.1021/ol1023757
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A practical method for the chemo- and diastereoselective allylation of alpha,beta-epoxy ketones has been developed by using the convenient air and moisture stable reagent potassium allyltrifluoroborate. Indium metal was found to promote addition in stoichiometric or catalytic amounts, to afford alpha,beta-epoxyhomoallylic tertiary alcohols in high yields and diastereoselectivities, without competing ring-scission of the epoxide.
引用
收藏
页码：5490 / 5493
页数：4
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