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A Samarium(II)-Mediated, Stereoselective Cyclization for the Synthesis of Azaspirocycles

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journal contribution
posted on 02.10.2008, 00:00 by Giuditta Guazzelli, Lorna A. Duffy, David J. Procter
Unsaturated keto-lactams undergo sequential conjugate reduction−aldol cyclization on treatment with SmI2 to give syn-spirocyclic pyrrolidinones and piperidinones containing vicinal, fully substituted stereocenters with complete diastereocontrol. The substituent on nitrogen and the lactam ring size have a marked impact on the efficiency of the spirocyclization.