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Synlett 1998; 1998(7): 765-767
DOI: 10.1055/s-1998-1770
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Anomalous Epoxide Formation Upon Wittig Olefination With 1-Iodoethyl Triphenylphosphonium Ylide

Hirokazu Arimoto* , Michael D. Kaufman, Kaoru Kobayashi, Yuping Qiu, Amos B. Smith, III
  • *Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, Pennsylvania 19104
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Publication Date:
31 December 2000 (online)

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Reaction of iodo Wittig ylide 1 with aldehyde 2 affords moderate yields of cis epoxides 6a and 7a, in addition to the expected olefin 3. A mechanism is proposed to account for both the high Z selectivity and the modest yield of olefin observed with this reagent.

Z-olefination - iodo Wittig ylids - α,β-epoxy phosphonium salts