Anomalous epoxide formation upon Wittig olefination with 1-iodoethyl triphenylphosphonium ylide

Hirokazu Arimoto, Michael D. Kaufman, Kaoru Kobayashi, Yuping Qiu, Amos B. Smith

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

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. Recently we reported the total synthesis of the immuno-suppressive/ antitumor agent (-)-discodermolide (4).1 A key component of our convergent synthetic strategy was the use of vinyl iodide 3 as the C(9)-C(14) subtarget (Scheme 1). Iodide 3 was conveniently prepared from aldehyde 2 employing the Zhao protocol for 2-iodo-2-alkene construction (Scheme 2).2 Accordingly, treatment of aldehyde 2 with ylide 1 afforded 3 as a 6:1 (Z/E) mixture of olefins in 41 % yield.1.

Original languageEnglish
Pages (from-to)765-767
Number of pages3
JournalSynlett
Issue number7
DOIs
Publication statusPublished - 1998 Jul
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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