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Oppolzer-type intramolecular Diels-Alder cycloadditions via isomerizations of allenamides.

ABSTRACT: A new approach to Oppolzer's intramolecular Diels-Alder cycloaddition (IMDA) through ?-isomerization of readily available N-tethered allenamides is described. These IMDA reactions are carried out in tandem with the allenamide isomerization or 1,3-H shift, leading to complex nitrogen heterocycles in a highly stereoselective manner.

SUBMITTER: Feltenberger JB

PROVIDER: S-EPMC3112474 | biostudies-literature | 2011 Jun

REPOSITORIES: biostudies-literature

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Oppolzer-type intramolecular Diels-Alder cycloadditions via isomerizations of allenamides.

Feltenberger John B JB Hsung Richard P RP

Organic letters 20110525 12

A new approach to Oppolzer's intramolecular Diels-Alder cycloaddition (IMDA) through γ-isomerization of readily available N-tethered allenamides is described. These IMDA reactions are carried out in tandem with the allenamide isomerization or 1,3-H shift, leading to complex nitrogen heterocycles in a highly stereoselective manner. ...[more]

PMID: 21612235

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