Rhodium-catalyzed synthesis of 1,2-dihydropyridine by a tandem reaction of 4-(1-acetoxyallyl)-1-sulfonyl-1,2,3-triazole
作者:Haican Dai、Sisi Yu、Wanli Cheng、Ze-Feng Xu、Chuan-Ying Li
DOI:10.1039/c7cc02521a
日期:——
A tandem reaction of 4-(1-acetoxyallyl)-1-sulfonyl-1,2,3-triazole including formation of α-imino rhodium carbene, 1,2-migration of an acetoxy group and six electron electrocyclic ring closure was reported. The migration of the OAc group with excellent chemoselectivity was the crucial process, leading to the formation of 1,2-dihydropyridine specifically in up to 90% yield. Several transformations of
据报道,4-(1-乙酰氧基烯丙基)-1-磺酰基-1,2,3-三唑的串联反应包括形成α-亚氨基铑卡宾,乙酰氧基的1,2-迁移和六个电子环的闭合。具有出色的化学选择性的OAc基团的迁移是关键过程,特别是导致1,2-二氢吡啶的形成,产率高达90%。还实现了二氢吡啶产物的几次转化,说明了该方案在有机合成中的潜力。基于对中间体的观察,提出了一个合理的机制。