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Synfacts 2009(2): 0167-0167  
DOI: 10.1055/s-0028-1087639
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Cyclohexenones via C-C Bond Activation of Allenyl Cyclobutanes

Contributor(s): Mark Lautens, Jacki Kitching
T. Seiser, N. Cramer*
ETH Zürich, Switzerland
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Publication History

Publication Date:
22 January 2009 (online)

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Significance

The rhodium(I)-catalyzed synthesis of highly substituted cyclohexanones, with quaternary stereogenic centers, from the corresponding allenyl tert-cyclobutanols is described. The proposed mechanism for this transformation involves enantioselective insertion into the C-C σ-bond of the cyclobutane. In addition, the enantiotopic C-C bond that is activated is reported to be determined by the ligand employed, allowing for access to either of the desired enantiomers.