Alkylation reactions using alpha-halolactams or lactam enolates derived from bicyclic lactam templates can proceed with high endo- or exo- diastereoselectivity respectively. In the latter case, stereochemical correction by means of enolate generation and hindered phenol quench is possible with moderate efficiency. This protocol has been applied to the synthesis of protected penmacric acid and its analogues.
The title compound, C13H16FNO4, consists of conventional, centrosymmetric carboxylate dimers. These dimers form infinite polymeric chains due to intermolecular N—H⋯O hydrogen bonding. The 2-fluorophenyl unit is disordered over two sets of sites with an ocupancy ratio of 0.915 (3):0.085 (3).
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.