Self-Assembled Bifunctional Catalyst for the Hydrophosphonylation of Aldehydes

Significance

Enantiomerically enriched α-hydroxy phosphonates and phosphonic acids are important intermediates in organic synthesis, and as a result have been subjected to considerable study including key contributions by Shibasaki, Katsuki and Feng. Herein, the authors combine the concepts of synergistic activation by two reactive centers and self-assembled catalyst to design new efficient self-assembled bifunctional catalysts for the asymmetric hydrophosphonylation of alkyl and aromatic aldehydes (up to 99% yield, up to >99% ee). The components of these self-assembled catalysts are commercially available which makes this protocol simple and accessible. For previous work see: T. Arai, M. Bougauchi, H. Sasai, M. Shibasaki J. Org. Chem. 1996, 61, 2926.