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Synfacts 2007(2): 0176-0176
DOI: 10.1055/s-2006-958973
DOI: 10.1055/s-2006-958973
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Cyclobutanes via a Stereoselective Ring Contraction
S. J. Meek, F. Pradaux, E. H. Demont, J. P. A. Harrity*
University of Sheffield and GlaxoSmithKline R&D, Harlow, UK
Further Information
Publication History
Publication Date:
23 January 2007 (online)
Significance
A Lewis acid catalyzed protocol was established to effect a ring contraction using the Nicholas reaction of a cobalt-alkyne complex. The Et2AlCl-mediated rearrangement furnishes exclusively the trans-1,2-functionalized cyclobutane 3 from 2,6-disubstituted dihydropyrans 2. The synthetic utility of the transformation was further demonstrated by a Ru-catalyzed ring-closing enyne metathesis to yield the [6.2.0] bicycle 7.