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Issue 9, 2017
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Catalytic [2 + 2 + 2] cycloaddition with indium(III)-activated formaldimines: a practical and selective access to hexahydropyrimidines and 1,3-diamines from alkenes

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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.

Graphical abstract: Catalytic [2 + 2 + 2] cycloaddition with indium(iii)-activated formaldimines: a practical and selective access to hexahydropyrimidines and 1,3-diamines from alkenes

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Publication details

The article was received on 08 Jun 2017, accepted on 20 Jul 2017 and first published on 24 Jul 2017


Article type: Edge Article
DOI: 10.1039/C7SC02576A
Citation: Chem. Sci., 2017,8, 6520-6524
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    Catalytic [2 + 2 + 2] cycloaddition with indium(III)-activated formaldimines: a practical and selective access to hexahydropyrimidines and 1,3-diamines from alkenes

    H. Zhou, H. H. Chaminda Lakmal, J. M. Baine, H. U. Valle, X. Xu and X. Cui, Chem. Sci., 2017, 8, 6520
    DOI: 10.1039/C7SC02576A

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