CAN-mediated tandem 5-exo-cyclisation of tertiary aminocyclopropanes: novel accelerative effect of an N-benzyl group for oxidative ring-opening

Abstract

Treatment of tertiary cyclopropylamines with cerium(IV) ammonium nitrate (CAN) gave ring-opened ketones and/or bicyclic secondary amines via an oxidative cyclopropane cleavage followed by a hydrogen abstraction or 5-exo radical cyclization: an N-benzyl group plays a crucial role in these reactions.

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