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Synlett 1995; 1995(7): 739-741
DOI: 10.1055/s-1995-5071
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Stereoselective Synthesis of Cyclopropanes via Homoallylic Participation

Tetsuya Nagasawa, Yasuhiko Handa, Yuka Onoguchi, Shigeru Ohba, Keisuke Suzuki*
  • *Department of Chemistry, Keio University, Hiyoshi, Yokohama 223, Japan
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Publication Date:
31 December 2000 (online)

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A facile method for synthesizing trans-disubstituted cyclopropanes is described. Upon conversion to the corresponding triflate, γ,γ-dimethyl homoallyl alcohols undergo smooth cyclization to give cyclopropanes in excellent trans selectivity and with an inversion of the hydroxyl center. Various functionalities could be introduced at the α-position of the newly formed cyclopropane ring. Alternatively, treatment of the intermediary triflate with triethylamine effects clean elimination of a triflic acid to give high yields of cyclopropanes with a 2-propenyl group, which are convertible to cyclopropyl methyl ketones by ozonolysis.

homoallyl alcohols - disubstituted cyclopropanes - homoallylic Participation - vinylcyclopropanes - cyclopropyl methyl ketones