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Thiourea-Catalyzed Enantioselective Hydrophosphonylation of Imines: Practical Access to Enantiomerically Enriched α-Amino Phosphonic Acids

Guy D. Joly and Eric N. Jacobsen*

*Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, Email: jacobsenchemistry.harvard.edu

G. D. Joly, E. N. Jacobson, J. Am. Chem. Soc., 2004, 126, 4102-4103.

DOI: 10.1021/ja0494398 (free Supporting Information)


Abstract

A chiral thiourea catalyzes the highly enantioselective hydrophosphonylation of a wide range of N-benzyl imines. Subsequent deprotection by hydrogenolysis provides access to free α-amino phosphonic acids in highly enantioenriched form.

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Key Words

α-Amino Phosphonates, Kabachnik-Fields Reaction, Organocatalysis


ID: J48-Y2004-1460