Stereocontrol in a combined allylic azide rearrangement and intramolecular Schmidt reaction.

ABSTRACT: 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.

SUBMITTER: Liu R 

PROVIDER: S-EPMC3340293 | biostudies-literature | 2012 Apr

REPOSITORIES: biostudies-literature