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Copper-Catalyzed Enantioselective Synthesis of trans-1-Alkyl-2-substituted Cyclopropanes via Tandem Conjugate Addition-Intramolecular Enolate Trapping

Tim den Hartog, Alena Rudolph, Beatriz Maci, Adriaan J. Minnaard* and Ben L. Feringa*

*Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands, Email:,

T. den Hartog, A. Rudolph, B. Maci, A. J. Minnaard, B. L. Feringa, J. Am. Chem. Soc., 2010, 132, 14349-14351.

DOI: 10.1021/ja105704m (free Supporting Information)


Cu-TolBINAP-catalyzed conjugate addition of alkyl Grignard reagents to 4-chloro-α,β-unsaturated esters, thioesters, and ketones leads to trans-1-alkyl-2-substituted cyclopropanes in good yield and high enantioselectivity. The versatility of this reaction is illustrated by the formation of key intermediates for the formal syntheses of cascarillic acid and grenadamide.

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ID: J48-Y2010-2820