Regio- and stereoselective construction of γ-butenolides through phosphine-catalyzed substitution of Morita-Baylis-Hillman acetates:: An organocatalytic allylic alkylation

被引:181
作者
Cho, CW [1 ]
Krische, MJ [1 ]
机构
[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA
关键词
D O I
10.1002/anie.200461381
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Hold the metal: Upon exposure of acetates 1 to substoichiometric quantities of triphenylphosphane in the presence of 2, regioselective metal-free allylic substitution occurs through a formal tandem SN2′-S N2′ substitution mechanism to provide γ-butenolides 3 with high levels of regio- and diastereocontrol (see scheme).
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页码:6689 / 6691
页数:3
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