Rhodium-catalyzed synthesis of 1,2-dihydropyridine by a tandem reaction of 4-(1-acetoxyallyl)-1-sulfonyl-1,2,3-triazole

Chemical Communications : Chem Comm
Haican DaiChuan-Ying Li

Abstract

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 the dihydropyridine product were also achieved illustrating the potential of the protocol in organic synthesis. Based on the observation of the intermediate, a plausible mechanism was proposed.

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Citations

May 20, 2020·Chemistry : a European Journal·Wenbo Li, Junliang Zhang
Dec 6, 2019·Chemical Science·Anton S MakarovA Stephen K Hashmi
Jun 20, 2020·Chemical Communications : Chem Comm·Tianhao LuChunsong Xie
Aug 24, 2021·Organic Letters·Nikolai Yu TiuftiakovNikolai V Rostovskii

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