Di- and Trisubstituted gamma-Lactams via Rh(II)-carbenoid Reaction of N-C-alpha-Branched, N-Bis(trimethylsilyl)methyl alpha-Diazoamides. Synthesis of (+/-)-alpha-Allokainic Acid

[摘要]：AcyclicN-C-alpha-branched, N-bis(trimethylsilyl)methyl (N-BTMSM) diazoamides undergo regio-, chemo-, and diastereoselective Rh(II)-carbenoid C-H insertion to give 4,5-disubstituted and 3,4,5-trisubstituted gamma-lactams. The conformational influence of the N-BTMSM group and the electronic: effect of the O-pivaloyl moiety of the C-alpha-oxymethylene unit are essential for the observed regioselectivity. The synthesis of alpha-allokainic acid demonstrates the utility of the method.

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