The copper(I) mediated reaction of nitrones and terminal acetylenes represents an attractive method of direct formation of the �-lactam ring. Reaction of sugar five-membered cyclic nitrones, readily available from pentofuranosides and 2-deoxypentofuranosides, with terminal acetylenes either achiral or bearing a stereogenic center proceeded in good yield and with high diastereoselectivity providing an attractive entry to carbapenam antibiotics of a potential biological activity. The stereochemical pathway of the reaction and influence of geometry and substitutions in one or both reactants on direction and magnitude of asymmetric induction will be discussed

Diastereoselective Kinugasa reaction as an entry to carbapenem antibiotics

244th National Meeting (2012)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.