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

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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 dap@chem.gu.se; fini_f@libero.it

J. Org. Chem., 2006, 71 (16), pp 6269–6272

DOI: 10.1021/jo060708h

Publication Date (Web): July 8, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

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

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Published In Issue August 04, 2006
Received April 3, 2006

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

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

Chiral Brønsted Acid Catalyzed Enantioselective Hydrophosphonylation of Imines: Asymmetric Synthesis of α-Amino Phosphonates

Chiral Brønsted Acid-Catalyzed Enantioselective α-Hydroxylation of β-Dicarbonyl Compounds

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

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