GENERATION OF 2-AZAPENTADIENYL ANIONS AND THEIR CYCLOADDITION WITH ALKENES - SYNTHESIS OF 2-ALKENYLPYRROLIDINES

被引：26

作者：

PEARSON, WH

JACOBS, VA

机构：

[1] Department of Chemistry, The University of Michigan, Ann Arbor

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 38期

关键词：

D O I：

10.1016/0040-4039(94)88209-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha,beta-Unsaturated imines 2 bearing an N-[1-(tri-n-butylstannyl)]alkyl group were transmetalated with n-BuLi to generate 2-azapentadienyl anions 3 which underwent [4 pi s+2 pi s] anionic cycloadditions with alkenes to afford 2-alkenylpyrrolidines 4 after workup with an electrophile. The alkenyl group could be oxidized to a diol, aldehyde, or ester. The imine 2 was found to undergo a [1,5]-sigmatropic rearrangement of the bi-n-butylstannyl group at 80 degrees C to provide the 2-azabutadiene 5.

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收藏

页码：7001 / 7004

页数：4

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