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Catalytic Synthesis of γ-Lactams via Direct Annulations of Enals and N-Sulfonylimines

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journal contribution
posted on 07.07.2005, 00:00 by Ming He, Jeffrey W. Bode
Cinnamaldehydes and N-sulfonylimines undergo direct annulations to cis-disubstituted γ-lactams via the intermediacy of catalytically generated homoenolates. Critical to the success of this process was overcoming inhibition of the N-heterocyclic carbene catalyst by the electrophilic imines. The overall process proceeds with good yields and diastereoselectivites and requires no stoichiometric reagents or additives.