Synfacts 2006(10): 1060-1060  
DOI: 10.1055/s-2006-949372
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Ring Opening of Cyclopropanes Catalyzed by an N-Heterocyclic Carbene

Contributor(s): Benjamin List, Daniela Kampen
S. S. Sohn, J. W. Bode*
University of California, Santa Barbara, USA
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Publikationsverlauf

Publikationsdatum:
21. September 2006 (online)

Significance

An organocatalytic ring opening of chiral enantioenriched cyclopropanes has been developed. The N-heterocyclic carbene generated in situ from triazolium chloride 1 (5 mol%) and DBU (20 mol%) mediates the redox reaction of trisubstituted formylcyclopropanes 2 with alcohols, thiols or water to give β-substituted carboxylic acid derivatives 3 in high yields and with preservation of the stereochemistry at the β-position. Furthermore, mechanistic considerations based on NMR spectroscopy are provided. Presumably the reaction proceeds via intermediates 4 and 5.