A New Chiral Auxiliary Derived from (2S)-Phenylglycinol: an Access to Enantiomerically Pure β-Amino Acids

Claude Agami; Sandrine Cheramy; Luc Dechoux; Catherine Kadouri-Puchot

doi:10.1055/s-1999-2704

Synlett 1999; 1999(6): 727-728
DOI: 10.1055/s-1999-2704

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A New Chiral Auxiliary Derived from (2S)-Phenylglycinol: an Access to Enantiomerically Pure β-Amino Acids

Claude Agami^* , Sandrine Cheramy, Luc Dechoux, Catherine Kadouri-Puchot

^*Laboratoire de Synthèse Asymétrique associé au CNRS, Université Pierre et Marie Curie, 4 place Jussieu, 75005 Paris, France; Fax +33 (1) 44 27 26 20; E-mail: dechoux@ccr.jussieu.fr

Abstract

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A new bicyclic heterocycle 3, which is potentially useful for the synthesis of β-amino acids, has been obtained from a reaction between (S)-phenylglycinol and cyanogen bromide followed by a condensation with methyl propiolate. Conjugate additions of different organocuprate reagents to this chiral Michael acceptor occurred with complete diastereoselectivity. An optically pure β amino acid was obtained in excellent yield from the masked chiral derivative 4a.

β-amino acids - chiral auxiliary - asymmetric synthesis - organocuprates

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