Rhodium-catalyzed asymmetric allylic substitution with boronic acid nucleophiles

被引：74

作者：

Menard, Frederic ^{[1
]}

Chapman, Timothy M. ^{[1
]}

Dockendorff, Chris ^{[1
]}

Lautens, Mark ^{[1
]}

机构：

[1] Univ Toronto, Davenport Labs, Dept Chem, Toronto, ON M5H 3H6, Canada

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 20期

关键词：

D O I：

10.1021/ol061777l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantio-, regio-, and diastereoselective rhodium(I)-catalyzed desymmetrization of a meso-cyclic allylic dicarbonate with organoboronic acid nucleophiles is described. The rhodium(I) catalyst formed in situ from [Rh(cod)OH](2) and Xyl-P-PHOS allowed the S(N)2' allylic substitution product to be obtained with a range of arylboronic acids in enantiomeric excesses of up to 92% with regioselectivities of up to > 20:1.

引用

页码：4569 / 4572

页数：4

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