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Synfacts 2011(6): 0635-0635  
DOI: 10.1055/s-0030-1260399
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Diastereo- and Enantioselective Synthesis of Pyrrolidines

Contributor(s): Mark Lautens, Hasnain A. Malik
A. Z. Gonzáles, D. Benitez, E. Tkatchouk, W. A. Goddard III, F. D. Toste*
University of California, Berkeley and California Institute of Technology, Pasadena, USA
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Publication History

Publication Date:
19 May 2011 (online)

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Significance

Functionalized pyrrolidines have drawn much interest due to the bioactive properties seen in natural and unnatural products bearing this moiety. As such, there is an important need for asymmetric methods for the synthesis of these structural motifs. The authors disclose a gold(I)-catalyzed diastereo- and enantioselective method for the synthesis of 3,4-substituted pyrrolidines and γ-lactones. Yields range from moderate to excellent, and enantioselectivities are generally good for the reported examples. A DFT study is performed to gain mechanistic insight into the methodology and the formal synthesis of (-)-isocyanometrine is undertaken to demonstrate the synthetic utility of the reaction.