Journal of the American Chemical Society, Vol.118, No.1, 111-116, 1996
Inversion of Stereochemistry in the Co-2(Co)(8)-Catalyzed Carbonylation of Aziridines to Beta-Lactams - The First Synthesis of Highly Strained Trans-Bicyclic Beta-Lactams
beta-Lactams were synthesized by the carbonylative ring expansion of aziridines catalyzed by dicobalt octacarbonyl under CO pressure. The active catalyst, cobalt tetracarbonyl anion, induces nucleophilic ring opening of the heterocycle, resulting in inversion of configuration. The regio- and stereospecificity of this reaction resulted in the synthesis of the first highly strained trans-7-azabicyclo[4-2-0]octan-8-one derivatives.
Keywords:TRANSFER CATALYZED CARBONYLATION;HALOGENATED IMINO COMPOUNDS;RING-EXPANSION;COBALT CARBONYL;CHLOROSULFONYL ISOCYANATE;STEREOSPECIFIC SYNTHESIS;ACIDS