Abstract
AbstractChemo-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.
Funder
National Science Foundation
Office of Research and Economic Development, Mississippi State University
Mississippi State University
Subject
Organic Chemistry,Catalysis
Cited by
1 articles.
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