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Synfacts 2006(7): 0706-0706  
DOI: 10.1055/s-2006-941863
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Cyclopentanes via Cyclopropane Ring Opening

Contributor(s): Mark Lautens, Andrew Martins
L. Liu, J. Montgomery*
University of Michigan, Ann Arbor and Wayne State University, Detroit, USA
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Publication History

Publication Date:
22 June 2006 (online)

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Significance

Using a Ni(0)/N-heterocyclic carbene catalyst system, cyclopropyl ketones were found to react and stereoselectively form substituted cyclopentanes. Cyclopropyl ketones and aldimines react with α,β-unsaturated ketones to generate ‘crossed’ addition products, whereas cyclopropyl ketones in the absence of enone dimerized to give similar products. This suggests that the enone is an intermediate in the reaction.