Cyclopropane-Aldehyde Annulations at Quaternary Donor Sites: Stereoselective Access to Highly Substituted Tetrahydrofurans

Austin G. Smith, Michael C. Slade and Jeffrey S. Johnson*

*Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, United States, Email: jsjunc.edu

A. G. Smith, M. C. Slade, J. S. Johnson, Org. Lett., 2011, 13, 1996-1999.

DOI: 10.1021/ol200395e

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Abstract

A diastereoselective synthesis of pentasubstituted tetrahydrofurans via a (3 + 2)-annulation of quaternary donor site cyclopropanes and aldehydes is catalyzed by Sn(OTf)₂, SnCl₄, or Hf(OTf)₄ in yields up to 95% and diastereomeric ratios as high as 99:1.

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Key Words

Tetrahydrofurans

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ID: J54-Y2011-1050