Catalytic Amidomethylative [2+2+2] Cycloaddition of Formaldimine and Styrenes toward N-Heterocycles

This paper is dedicated to the 20th anniversary of the Professor Peter Zhang group.

Abstract

Chemo-switchable catalytic [2+2+2] cycloaddition of alkenes with formaldimines is reported. Bis(tosylamido)methane (BTM) and 1,2-ditosyl-1,2-diazetidine (DTD), two bench-stable precursors for highly reactive tosylformaldimine, have been identified to be effective. BTM worked as a selective releaser of the formaldimine for catalytic [2+2+2] reactions toward hexahydropyrimidine products via a presumable ‘imine–alkene–imine’ addition. A unique catalytic retro-[2+2] reaction of DTD was used and has enabled a proposed ‘imine–alkene–alkene’ pathway with high chemoselectivity for the synthesis of 2,4-di­arylpiperidine derivatives. The two alternative processes are catalyzed by the simple and environmentally benign catalysts InCl₃ and FeBr₂, respectively.

Key words

[2+2+2] cycloaddition - aza-Prins reaction - chemoselectivity - formaldimines - N-heterocycles - diazetidine - controlled release

Publication History

Received: 15 October 2021

Accepted after revision: 01 December 2021

Accepted Manuscript online:
01 December 2021

Article published online:
27 January 2022

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