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Enantioselective formal aza-Diels-Alder reactions of enones with cyclic imines catalyzed by primary aminothioureas.

ABSTRACT: A highly enantio- and diastereoselective synthesis of indolo- and benzoquinolizidine compounds has been developed through the formal aza-Diels-Alder reaction of enones with cyclic imines. This transformation is catalyzed by a new bifunctional primary aminothiourea that achieves simultaneous activation of both the enone and imine reaction components.

SUBMITTER: Lalonde MP

PROVIDER: S-EPMC3566267 | biostudies-literature | 2013 Feb

REPOSITORIES: biostudies-literature

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Enantioselective formal aza-Diels-Alder reactions of enones with cyclic imines catalyzed by primary aminothioureas.

Lalonde Mathieu P MP McGowan Meredeth A MA Rajapaksa Naomi S NS Jacobsen Eric N EN

Journal of the American Chemical Society 20130128 5

A highly enantio- and diastereoselective synthesis of indolo- and benzoquinolizidine compounds has been developed through the formal aza-Diels-Alder reaction of enones with cyclic imines. This transformation is catalyzed by a new bifunctional primary aminothiourea that achieves simultaneous activation of both the enone and imine reaction components. ...[more]

PMID: 23321009

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