Stereoselective synthesis of N-protected pyrrolidines via Pd-catalyzed reactions of γ-(N-acylamino) alkenes and γ-(N-Boc-amino) alkenes with aryl bromides
Myra Beaudoin Bertrand and John P. Wolfe*
*Department of Chemistry, University of Michigan, 930 N. University Avenue,
Ann Arbor, MI 48109-1055, USA, Email: jpwolfe
umich.edu
M. B. Bertrand, J. P. Wolfe, Tetrahedron, 2005, 61, 6447-6459.
DOI: 10.1016/j.tet.2005.03.110
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Abstract
The stereoselective synthesis of N-acyl- and N-Boc-protected pyrrolidines via Pd-catalyzed reactions of γ-(N-acylamino) alkenes and γ-(N-Boc-amino) alkenes with aryl bromides proceeds with generally high levels of diastereoselectivity by formation of two bonds in a single operation.
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proposed mechanism
Mild Conditions for the Synthesis of Functionalized Pyrrolidines via Pd-Catalyzed Carboamination Reactions
M. B. Bertrand, M. L. Leathen, J. P. Wolfe, Org. Lett., 2007, 9, 457-460. DOI
Key Words
Stereoselective synthesis, Pyrrolidines, Diastereoselectivity, Palladium, Arylhalide
ID: J72-Y2005-2970
