Volume 46, Issue 32 pp. 6123-6125

Communication

Dynamic Kinetic Asymmetric Allylic Amination and Acyl Migration of Vinyl Aziridines with Imido Carboxylates^†

Barry M. Trost Prof.,

Barry M. Trost Prof.

[email protected]

Department of Chemistry, Stanford University, Stanford CA 94305, USA, Fax: (+1) 650-725-0002

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Daniel R. Fandrick Dr.,

Daniel R. Fandrick Dr.

Department of Chemistry, Stanford University, Stanford CA 94305, USA, Fax: (+1) 650-725-0002

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Tobias Brodmann,

Tobias Brodmann

Department of Chemistry, Stanford University, Stanford CA 94305, USA, Fax: (+1) 650-725-0002

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Dylan T. Stiles,

Dylan T. Stiles

Department of Chemistry, Stanford University, Stanford CA 94305, USA, Fax: (+1) 650-725-0002

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Barry M. Trost Prof.,

Barry M. Trost Prof.

[email protected]

Department of Chemistry, Stanford University, Stanford CA 94305, USA, Fax: (+1) 650-725-0002

Search for more papers by this author

Daniel R. Fandrick Dr.,

Daniel R. Fandrick Dr.

Department of Chemistry, Stanford University, Stanford CA 94305, USA, Fax: (+1) 650-725-0002

Search for more papers by this author

Tobias Brodmann,

Tobias Brodmann

Department of Chemistry, Stanford University, Stanford CA 94305, USA, Fax: (+1) 650-725-0002

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Dylan T. Stiles,

Dylan T. Stiles

Department of Chemistry, Stanford University, Stanford CA 94305, USA, Fax: (+1) 650-725-0002

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First published: 03 August 2007

https://doi.org/10.1002/anie.200700835

Citations: 93

^†

We thank the National Science Foundation and the National Institutes of Health, General Medical Sciences Institute (GM-13598), for their generous support of our programs. Mass spectra were provided by the Mass Spectrometry Facility of the University of California-San Francisco, supported by NIH Division of Research Resources.

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Graphical Abstract

An atom-economical method has been developed for the preparation of chiral vicinal diamines through a dynamic kinetic asymmetric allylic amination and acyl-group migration of vinyl aziridines with imido carboxylates. Application of the asymmetric transformation enabled the concise synthesis of the azepane core 1 of (+)-balanol and its syn analogue.

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Volume46, Issue32

August 13, 2007

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Dynamic Kinetic Asymmetric Allylic Amination and Acyl Migration of Vinyl Aziridines with Imido Carboxylates^†

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Dynamic Kinetic Asymmetric Allylic Amination and Acyl Migration of Vinyl Aziridines with Imido Carboxylates^†