Improved E-selectivity in the Wittig reaction of stabilized ylides with α-alkoxyaldehydes and sugar lactols

被引：61

作者：

Harcken, C ^{[1
]}

Martin, SF ^{[1
]}

机构：

[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 22期

关键词：

D O I：

10.1021/ol016729+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The Wittig reactions of alpha -alkoxyaldehydes and sugar lactols with stabilized ylides such as (alkoxycarbonylmethylene)triphenylphosphoranes typically proceed with low E-selectivities. However, we have discovered that the reaction of such aldehydes with (methoxycarbonylmethylene)tributylphosphorane in toluene in the presence of catalytic amounts of benzoic acid proceeds to give the E-alpha,beta -unsaturated esters with high selectivities and in high yields.

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页码：3591 / 3593

页数：3

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