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

[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.

[发布日期] 1994-09-19