Chiral NHC-catalyzed 1,3-dipolar [3 + 2] cycloaddition of azomethine imines with α-chloroaldehydes for the synthesis of bicyclic pyrazolidinones.

Abstract

A chiral N-heterocyclic carbene (NHC)-catalyzed 1,3-dipolar [3 + 2] cycloaddition reaction of 3-oxopyrazolidin-1-ium-2-ides and α-chloroaldehydes was developed for the synthesis of pyrazolo[1,2-a]pyrazole-1,7-diones in moderate to good yields (up to 76%) with good enantioselectivities (up to 98% ee) and diastereoselectivities (up to 8 : 1 dr).