Catalytic asymmetric cyclopropanation of sulfoxonium ylides catalyzed by a chiral-at-metal rhodium complex?

Organic Chemistry Frontiers Pub Date: 2022-08-11 DOI: 10.1039/D2QO01068B

Abstract

An efficient asymmetric cyclopropanation of sulfoxonium ylides with α,β-unsaturated 2-acyl imidazoles catalyzed by a chiral-at-metal rhodium complex has been developed. The enantioenriched cyclopropane derivatives bearing three contiguous tertiary stereocenters were obtained in generally high yields (up to 98%) with excellent stereoselectivities (up to >20?:?1 dr, >99% ee). Remarkably, as low as 0.1 mol% of the chiral Rh(III) complex can realize a scale-up reaction with excellent yield and enantioselectivity.

Graphical abstract: Catalytic asymmetric cyclopropanation of sulfoxonium ylides catalyzed by a chiral-at-metal rhodium complex
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