Synthesis
DOI: 10.1055/a-1710-7256
feature

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

Hetti Handi Chaminda Lakmal
1  Chemistry, Mississippi State University, Mississippi State, United States (Ringgold ID: RIN5547)
,
Jacob Istre
1  Chemistry, Mississippi State University, Mississippi State, United States (Ringgold ID: RIN5547)
,
Xiaolin Qian
1  Chemistry, Mississippi State University, Mississippi State, United States (Ringgold ID: RIN5547)
,
1  Chemistry, Mississippi State University, Mississippi State, United States (Ringgold ID: RIN5547)
,
Henry U Valle
1  Chemistry, Mississippi State University, Mississippi State, United States (Ringgold ID: RIN5547)
,
Xue Xu
1  Chemistry, Mississippi State University, Mississippi State, United States (Ringgold ID: RIN5547)
,
2  Chemistry, Mississippi State University, Mississippi State, United States (Ringgold ID: RIN5547)
› Author Affiliations
Supported by: National Science Foundation CHE-1945425

Chemo-switchable catalytic [2+2+2] cycloaddition of alkenes with formaldimines has been 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-diarylpyperidine derivatives. The two alternative processes were catalyzed by simple and environmentally benign catalysts InCl3 and FeBr2, respectively.



Publication History

Received: 15 October 2021

Accepted after revision: 01 December 2021

Publication Date:
01 December 2021 (online)

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