Catalytic [2 + 2 + 2] cycloaddition with indium(iii)-activated formaldimines: a practical and selective access to
Hui Zhou1, Hetti Handi Chaminda Lakmal1, Jonathan M Baine1
1Department of Chemistry , Mississippi State University , Mississippi State , MS 39762 , USA .
Abstract:
Catalytic [2 + 2 + 2] cycloaddition with imines has, for the first time, been developed as a practical and selective approach for direct construction of hexahydropyrimidine derivatives from various alkenes. With formaldimines as reagents and simple InCl3 as the catalyst, this ionic [2 + 2 + 2] approach is applicable for a wide scope of alkenes and allenes with various electronic and steric properties, as well as substitution patterns. Through facile hydrolysis of the resulting hexahydropyrimidines, this catalytic process also provides a new synthetic strategy for the aminomethylamination of alkenes and allenes to practically access 1,3-diamine derivatives.
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