Volume 43, Issue 27 pp. 3605-3608

Communication

Palladium-Catalyzed Synthesis of N-Aryl Pyrrolidines from γ-(N-Arylamino) Alkenes: Evidence for Chemoselective Alkene Insertion into PdN Bonds^†

Joshua E. Ney,

Joshua E. Ney

University of Michigan, Department of Chemistry, Ann Arbor, MI 48109-1055, USA, Fax: (+1) 734-763-2307

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John P. Wolfe Prof.,

John P. Wolfe Prof.

[email protected]

University of Michigan, Department of Chemistry, Ann Arbor, MI 48109-1055, USA, Fax: (+1) 734-763-2307

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Joshua E. Ney,

Joshua E. Ney

University of Michigan, Department of Chemistry, Ann Arbor, MI 48109-1055, USA, Fax: (+1) 734-763-2307

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John P. Wolfe Prof.,

John P. Wolfe Prof.

[email protected]

University of Michigan, Department of Chemistry, Ann Arbor, MI 48109-1055, USA, Fax: (+1) 734-763-2307

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First published: 29 June 2004

https://doi.org/10.1002/anie.200460060

Citations: 171

^†

This research was supported by the University of Michigan. J.P.W. thanks The Dreyfus Foundation for a New Faculty Award and Research Corporation for an Innovation Award. J.E.N. thanks the University of Michigan for a Regents Fellowship. Additional unrestricted support was provided by Eli Lilly, 3M, and Amgen.

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Graphical Abstract

The formation of a CC and a CN bond in a reaction between γ-(N-arylamino) alkenes and aryl bromides results in the stereoselective synthesis of substituted pyrrolidine derivatives (see scheme). Preliminary studies suggest these reactions proceed by intramolecular alkene insertion into the PdN bond of intermediate [Pd(Ar)(amido)] complexes. dba=dibenzylideneacetone, dppb=1,3-bis(diphenylphosphanyl)butane.

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Volume43, Issue27

July 5, 2004

Pages 3605-3608

Palladium-Catalyzed Synthesis of N-Aryl Pyrrolidines from γ-(N-Arylamino) Alkenes: Evidence for Chemoselective Alkene Insertion into PdN Bonds^†

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Palladium-Catalyzed Synthesis of N-Aryl Pyrrolidines from γ-(N-Arylamino) Alkenes: Evidence for Chemoselective Alkene Insertion into PdN Bonds†

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Palladium-Catalyzed Synthesis of N-Aryl Pyrrolidines from γ-(N-Arylamino) Alkenes: Evidence for Chemoselective Alkene Insertion into PdN Bonds^†