Stereoselective Synthesis of Fused Bicyclic beta-Lactams through Radical Cyclization of Enyne-2-azetidinones(1).

A convenient, stereoselective entry to racemic and enantiomerically pure fused bicyclic beta-lactams has been developed that involves the radical-mediated cycloisomerization of easily available monocyclic enyne-beta-lactams as the key synthetic step. These compounds are obtained provided that an activated double bond is present as a radical acceptor. In the absence of this condition, new forms of reactivity were observed, including C3-C4 bond cleavage of the beta-lactam ring to yield tetrahydropyridine derivatives and 1,5-radical translocation to yield new bicyclic derivatives.