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

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Abstract
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.

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