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Synfacts 2006(2): 0140-0140  
DOI: 10.1055/s-2005-924772
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantiospecific Synthesis of Tetrahydrofurans via Cyclopropane Cycloaddition

Contributor(s): Mark Lautens, Andrew Martins
P. D. Pohlhaus, J. S. Johnson*
University of North Carolina at Chapel Hill, USA
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Publication History

Publication Date:
23 January 2006 (online)

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Significance

Cyclopropanes have received recent attention as partners in cycloaddition reactions. In the presence of Sn(II) or Sn(IV), chiral donor-acceptor cyclopropanes undergo a [3+2] cycloaddition with a variety of aldehydes to generate chiral tetrahydrofuran products. Electron-rich aldehydes afford the best results, and good results were obtained with both aromatic and aliphatic, enolizable aldehydes.