[2,3]-Wittig sigmatropic rearrangement of γ-allyloxy-β-enaminoesters

被引:0
|
作者
Pévet, I [1 ]
Meyer, C [1 ]
Cossy, J [1 ]
机构
[1] ESPCI, CNRS, Chim Organ Lab, F-75231 Paris 05, France
关键词
beta-ketoesters; beta-enaminoesters; lithiation; Wittig rearrangement; lactones;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The dianions derived from gamma-allyloxy-beta-enaminoesters undergo a [2,3]-Wittig sigmatropic rearrangement leading to gamma-hydroxy-beta-enaminoester derivatives, which can be subsequently lactonized to the corresponding 4-aminofuran-2(5H)-ones.
引用
收藏
页码:663 / 666
页数:4
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