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

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;

Abstract

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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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References

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