Organic Chemistry Portal

Abstracts

Search:

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: b.l.feringarug.nl, a.j.minnaardrug.nl

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)


Abstract

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.


see article for more examples



Key Words

Cyclopropanes


ID: J48-Y2010-2820