Control of the regioselectivity of N-nucleophile addition to N-carbonyl protected dehydroalanines: a model for the ammonia-lyase enzymes

Abstract

The regioselectivity of the addition of N-nucleophiles to N-carbonyl protected dehydroalanine derivatives, β-conjugate addition vs. α-imine capture, can be controlled completely by varying the N-protecting group, or, the carboxy protecting group thereby providing a model for the chemistry of dehydroalanine residues within enzymes.