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Chiral Pyrrolidines and Piperidines from Enantioselective Rhodium-Catalyzed Cascade Arylative Cyclization

Fabien Serpier, Benjamin Flamme, Jean-Louis Brayer, Benoît Folléas and Sylvain Darses*

*PSL Research University, Chimie ParisTech - CNRS, Institut de Recherche de Chimie Paris, 11 rue Pierre et Marie Curie, 75005, Paris, France, Email: sylvain.darseschimie-paristech.fr

F. Serpier, B. Flamme, J.-L. Brayer, B. Folléas, S. Darses, Org. Lett., 2015, 17, 1720-1723.

DOI: 10.1021/acs.orglett.5b00493 (free Supporting Information)


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Abstract

A rhodium-catalyzed asymmetric arylative cyclization of nitrogen-tethered alkyne-enoate with arylboronic acids, in which two new carbon-carbon bonds and one stereocenter are formed, provides access to pyrrolidines and piperidines with good enantioselectivities by to the use of a C1-symmetric chiral monosubstituted diene ligands.

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Key Words

pyrrolidines


ID: J54-Y2015