Enantioselective allylation of β,γ-unsaturated aldehydes generated via lewis acid induced rearrangement of 2-vinyloxiranes

被引：36

作者：

Lautens, M ^{[1
]}

Maddess, ML ^{[1
]}

Sauer, EL ^{[1
]}

Ouellet, SG ^{[1
]}

机构：

[1] Univ Toronto, Davenport Res Labs, Dept Chem, Toronto, ON M5S 3H6, Canada

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 01期

关键词：

D O I：

10.1021/ol016946a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

GRAPHICS 2-Vinyloxiranes have been found to be excellent surrogates to beta,gamma-unsaturated aldehydes. These valuable electrophiles, generated in situ by treatment of a 2-vinyloxirane with a catalytic amount of Sc(OTf)(3), are effectively trapped by the chiral allylating agents based on alpha-pinene, affording bishomoallylic alcohols in high yield and excellent selectivity.

引用

页码：83 / 86

页数：4

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