Catalytic enantioselective hydrophosphonylation of aldehydes and imines

Abstract

In this review, recent advances in catalytic asymmetric hydrophosphonylation of aldehydes and imines are discussed. We also summarize several proposed mechanisms for the different possibilities of asymmetric induction and the application of this catalytic methodology to the enantioselective synthesis of α-amino and α-hydroxy phosphonates. A variety of metal-based chiral catalysts as well as several organic catalysts have been exploited as suitable systems for the preparation of enantiomerically pure phosphonates. The recent evolution and future trends of those and other catalytic systems are described. 1 Introduction 2 Catalytic Enantioselective Addition Reaction of Phosphites to Aldehydes 2.1 Metal-Catalyzed Phospho-Aldol Reaction 2.2 Organocatalytic Phospho-Aldol Reaction 3 Catalytic Enantioselective Addition Reaction of Phosphites to Imines 3.1 Metal-Catalyzed Hydrophosphonylation Reaction of Imines 3.2 Organocatalytic Hydrophosphonylation of Imines 4 Concluding Remarks. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.