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

Daniel Pettersen,* Mauro Marcolini, Luca Bernardi, Francesco Fini, Raquel P. Herrera, Valentina Sgarzani and Alfredo Ricci

*Department of Organic Chemistry "A. Mangini", University of Bologna, V. Risorgimento 4, 40136 Bologna, Italy, Email: dapchem.gu.se

D. Pettersen, M. Marcolini, L. Bernardi, F. Fini, R. P. Herrera, V. Sgarzani, A. Ricci, J. Org. Chem., 2006, 71, 6269-6272.

DOI: 10.1021/jo060708h (free Supporting Information)


Abstract

A simple, efficient, quinine-catalyzed, enantioselective hydrophosphonylation of N-Boc protected imines with diethyl poshphite gives enantiomerically enriched α-amino phosphonates in good yields.

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proposed mechanism



Key Words

α-Amino Phosphonates, Kabachnik-Fields Reaction, Organocatalysis


ID: J42-Y2006-2410