Derivatives of 2-amino-4-pentenoic acid (allylglycine) were efficiently resolved using Subtilisin or acylase. The side-chain unsaturated bond of the enantiomerically pure amino acid with tert-butoxycarbonyl (Boc) protection was smoothly epoxidized with m- chloroperbenzoic acid. When the Boc protection of the amino group was removed, the amino group intramolecularly attacked the side-chain epoxide, generating compounds ...
[Lloyd, Richard C.; Smith, Mark E. B.; Brick, Dean; Taylor, Stephen J. C.; Chaplin, David A.; McCague, Raymond Organic Process Research and Development, 2002 , vol. 6, # 6 p. 762 - 766]