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
see article for more reactions
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.
see article for more examples
proposed mechanism
Use of Aryl Chlorides as Electrophiles in Pd-Catalyzed Alkene Difunctionalization Reactions
B. R. Rosen, J. E. Ney, J. P. Wolfe, J. Org. Chem., 2010, 75, 2756-2759.
Key Words
Stereoselective synthesis, Pyrrolidines, Diastereoselectivity, Palladium, Arylhalide
ID: J72-Y2005-2970
