Direct access to enantiomerically enriched alpha-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

doi:10.1021/jo060708h

Direct access to enantiomerically enriched alpha-amino phosphonic acid derivatives by organocatalytic asymmetric hydrophosphonylation of imines

J Org Chem. 2006 Aug 4;71(16):6269-72. doi: 10.1021/jo060708h.

Authors

Daniel Pettersen¹, Mauro Marcolini, Luca Bernardi, Francesco Fini, Raquel P Herrera, Valentina Sgarzani, Alfredo Ricci

Affiliation

¹ Department of Organic Chemistry "A. Mangini", University of Bologna, V. Risorgimento 4, 40136 Bologna, Italy. dap@chem.gu.se

PMID: 16872218
DOI: 10.1021/jo060708h

Abstract

A simple and efficient organocatalytic enantioselective hydrophosphonylation of imines to enantiomerically enriched alpha-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, alpha-amino phosphonates are obtained in moderate to good yields and with up to 94% ee.