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Synfacts 2008(2): 0182-0182  
DOI: 10.1055/s-2007-992494
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Preparation of Substituted Pyrrolidines by Diastereoselective Reduction

Contributor(s): Mark Lautens, Frédéric Ménard
C. Jiang, A. J. Frontier*
University of Rochester, USA
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Publication History

Publication Date:
23 January 2008 (online)

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Significance

A very simple strategy was used to provide highly substituted pyrrolidines. With this approach, up to four stereogenic centers are created with good diastereomeric control from planar molecules. Previous attempts at hydrogenating pyrroles were unselective. The key for a successful reaction is the presence of an alcohol or amine group α to the pyrrole, at the 2-position.