High trans selectivity in the copper bis(oxazoline)-catalyzed asymmetric cyclopropanation of olefins by (trimethylsilyl)diazomethane

Abstract

Copper(I) bis(oxazoline) species are among the most enantioselective cyclopropanation catalysts that have been reported, although these catalysts generally give low diastereoselectivities. We have observed greatly improved diastereoselectivities using (trimethylsilyl)diazomethane as the carbon source. We have also identified several bis(oxazoline) species that also give comparable or higher enantioselectivities with (trimethylsilyl)diazomethane compared to the more readily available ethyl diazoacetate. The application of this methodology to several olefins has been explored.