Ionic [2 + 2 + 2] process as a new way to construct saturated N-heterocycles

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The Cui Group has developed a practical and direct synthetic access to saturated cyclic compounds by catalytic [2+2+2] reactions of simple alkenes. Indium-catalyzed [2+2+2] cycloaddition has been proven effective for the direct construction of hexahydropyrimidines, a class of pharmaceutically related compounds, from both alkenes and allenes. This method provides a new way to solve the challenge of catalytic [2+2+2] reactions with three double bond systems. Through facile hydrolysis of the resulting hexahydropyrimidines, this catalytic process also provides a new synthetic strategy for the aminomethylamination of alkenes and allenes to access 1,3-diamine derivatives.

Zhou, H.; Chaminda Lakmal, H. H.; Baine, M. J.; Valle, U. H.; Xu, X.; Cui, X. "Catalytic [2 + 2 + 2] cycloaddition with indium(III)-activated formaldimines: a practical and selective access to hexahydropyrimidines and 1,3-diamines from alkenes" Chem. Sci. 2017, 8, 6520. (doi)


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