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Synfacts 2009(8): 0889-0889
DOI: 10.1055/s-0029-1217447
DOI: 10.1055/s-0029-1217447
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Chiral Seven-Membered Bicycles through Sigmatropic Rearrangements
T. V. Ovaska*, J. A. Sullivan, S. I. Ovaska, J. B. Winegrad, J. D. Fair
Connecticut College, New London, USA
Further Information
Publication History
Publication Date:
23 July 2009 (online)
Significance
The authors report an application of the Claisen rearrangement in the synthesis of chiral bicyclic cycloheptenone derivatives 2. While the Claisen rearrangement is an extensively studied reaction (see Review below), this is reported to be the first asymmetric application towards the cycloheptenone system. Through transfer of the starting material chirality up to two stereocenters can be constructed in decent enantio- and diastereoselectivity.
Review: M. A. Battiste, P. M. Pelphrey, D. L. Wright Chem. Eur. J. 2006, 12, 3438-3447.