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Synfacts 2008(9): 0951-0951  
DOI: 10.1055/s-2008-1078643
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Substituted Tetrahydrofurans by [3+2] Cycloadditions

Contributor(s): Mark Lautens, Frédéric Ménard
A. T. Parsons, M. J. Campbell, J. S. Johnson*
University of North Carolina at Chapel Hill, USA
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Publikationsdatum:
22. August 2008 (online)

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Significance

The common occurrence of various THF substitution patterns in biologically active compounds makes the advent of new efficient methods to prepare these structures welcome. The authors report a simple procedure to synthesize 2,3,5-trisubstituted tetrahydrofurans from simple starting materials. Vinylcyclopropane (VCP) was prepared in one step from malonate and 1,4-dibromo-2-butene. Low catalyst loadings can be used to obtain 2,5-cis-tetrahydrofurans.