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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

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

Liu Ruzhang R Gutierrez Osvaldo O Tantillo Dean J DJ Aubé Jeffrey J

Journal of the American Chemical Society 20120410 15

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. ...[more]

PMID: 22490078

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