Palladium-catalyzed formation and stereoselective isomerization of 5- vinyloxazolines. Application to the formal synthesis of (S,S)-4-amino-3- hydroxy-5-phenylpentanoic acid

Article abstract of DOI:10.1016/S0040-4039(98)00534-6

Vinyloxazolidinones have been found to undergo Pd(0)-catalyzed ionization followed by loss of carbon dioxide and subsequent cyclization to form vinyloxazolines. The reaction occurred under mild conditions, and enhancement of diastereomeric ratios with chiral substrates was obtained. 4- Benzyl-5-vinyloxazoline prepared by this method has been utilized in the stereoselective synthesis of (S,S)-4-amino-3-hydroxy-5-phenylpentanoic acid (AHPPA).