Investigation of ligand steric effects on a highly cis-selective Rh(i) cyclopropanation catalyst

Abstract

Four new Rh(I) complexes bearing chelating imine-functionalized N-heterocyclic carbene ligands have been synthesized and characterized. The catalytic activity of these new Rh(I) complexes has been tested in the cyclopropanation reaction between ethyl diazoacetate and styrene. One of the new complexes, having ethyl groups on the ligand N-aryl ring, exhibited a reactivity and a cis-diastereoselectivity that were comparable to our previously reported Rh(I) cyclopropanation catalyst of this type, and a higher yield and cis-diastereoselectivity were obtained at lower catalyst loadings and higher temperatures. The other new Rh(I) complexes were found to be inferior to the previously reported Rh(I) cyclopropanation catalyst. The catalytic study gave important information about the effect that changing the steric requirements of the substituents at the ligand system has on the efficiency and cis-diastereoselectivity of the complexes as cyclopropanation catalysts.