ABSTRACT
Studies describe formation of the lithium enolate of N-(4-methoxybenzyloxy)azetidin-2-one (1) and characterization of representative aldol reactions with aldehydes and ketones. Diastereoselectivity features the production of anti-aldol adducts from α,ß-unsaturated ketones and α-branched aliphatic aldehydes. The stereoselectivity is rationalized via closed, six-membered transition-state arrangements leading to the formation of Felkin-Anh and anti-Felkin products. Examples illustrate the direct incorporation of monocyclic ß-lactams into a variety of molecular architectures. The utility of 1 as an enolate synthon of homoglycine (ß-alanine) is illustrated by the efficient synthesis of novel ß-amino acid derivatives, including complex 4-hydroxy-2-pyridinones.
