Asymmetric Synthesis of (R)- and (S)-α-Amino-3-piperidinylphosphonic Acids via Phosphite Addition to Iminium Ions

Nicolas Louaisil; Nicolas Rabasso; Antoine Fadel

doi:10.1055/s-2006-958952

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Synthesis 2007(2): 289-293
DOI: 10.1055/s-2006-958952

PAPER

Asymmetric Synthesis of ( R )- and ( S )-α-Amino-3-piperidinylphosphonic Acids via Phosphite Addition to Iminium Ions

Nicolas Louaisil, Nicolas Rabasso, Antoine Fadel*
Laboratoire de Synthèse Organique et Méthodologie, UMR 8182, Institut de Chimie Moléculaire et des Matériaux d’Orsay, Bât. 420, Université de Paris-Sud, 91405 Orsay, France
Fax: +33(1)69156278; e-Mail: antfadel@icmo.u-psud.fr;

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Publication History

Received 26 September 2006
Publication Date:
21 December 2006 (online)

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Abstract

α-Amino-3-piperidinylphosphonates were conveniently prepared from 3-piperidinone, by nucleophilic addition of phosphite to the iminium ion formed by in situ condensation of this ketone with chiral benzylic amines. Subsequent deprotection of N-Boc group, cleavage of the benzyl groups and acidic hydrolysis of the resulting α-amino-3-piperidinylphosphonates gave, in a four-step sequence from piperidinone, the enantiopure α-amino-3-piperidinylphosphonic acids. The absolute configuration has been established by X-ray crystal structure analysis of the N-(4-nitro-benzoyl)aminophosphonate derivative.

Key words

amino acids - heterocycles - piperidines - asymmetric synthesis - addition reaction

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Crystallographic data for compound (+)-11B has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 614693. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1233)336033; E-mail: deposit@ccdc.cam.ac.uk.