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Stereocontrol in a Combined Allylic Azide Rearrangement and Intramolecular Schmidt Reaction

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journal contribution
posted on 2012-04-18, 00:00 authored by Ruzhang Liu, Osvaldo Gutierrez, Dean J. Tantillo, Jeffrey Aubé
Pre-equilibration of an interconverting set of isomeric allylic azides is coupled with an intramolecular Schmidt reaction to afford substituted lactams stereoselectively. The effect of substitution and a preliminary mechanistic study are reported. The synthetic potential of this method is demonstrated in the context of an enantioselective synthesis of an advanced intermediate leading toward pinnaic acid.