Direct Access to Enantiomerically Enriched alfa-Amino Phosphonic Acid Derivatives by Organocatalytic Asymmetric Hydrophosphonylation of Imines

Daniel Pettersen, Mauro Marcolini, Luca Bernardi, Francesco Fini, Raquel P. Herrera, Valentina Sgarzani, Alfredo Ricci. Direct Access to Enantiomerically Enriched alfa-Amino Phosphonic Acid Derivatives by Organocatalytic Asymmetric Hydrophosphonylation of Imines. J. Org. Chem.. 2006, Vol. 71 / 2006, p. 6269-2006.

<p>A simple and efficient organocatalytic enantioselective hydrophosphonylation of imines to enantiomerically enriched a-amino phosphonates is reported. By using 10 mol % of quinine as the catalyst in the enantioselective addition of diethyl phosphite to N-Boc protected imines, a-amino phosphonates are obtained in moderate to good yields and with up to 94% ee.</p>