Enantio- and Diastereocontrol in Intermolecular Cyclopropanation Reaction of Styrene Catalyzed by Dirhodium(II) Complexes with Bulky <i>ortho</i>-Metalated Aryl Phosphines: Catalysis in Water as Solvent. Study of a (+)-Nonlinear Effect

Abstract

Enantiomerically pure dirhodium(II) complexes with ortho-metalated para-substituted aryl phosphines have been shown to lead to an enantio- and diastereoselective cyclopropanation of styrene with ethyl diazoacetate. Enantioselectivities up to 91% and diastereoselectivities up to 90% are observed for ethyl cis-2-phenylcyclopropanecarboxylate. High enantio- and diastereoselectivities are observed for the synthesis of ethyl cis-2-phenylcyclopropanecarboxylate using water as solvent. Additionally, a (+)-nonlinear effect, (+)-NLE, has been observed and studied in the asymmetric catalytic reaction developed in n-pentane.