Diastereoselective iodocarbocyclization reaction of 2- or 3-oxy-4-pentenylmalonate derivatives

Tadashi Inoue, Osamu Kitagawa, Yoko Oda, Takeo Taguchi

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

1,2- Or 1,3-asymmetric induction in the iodocarbocyclization reaction of 4-pentenylmalonate derivatives having a stereogenic center at an allylic or a homoallylic position has been investigated. The iodocarbocyclization reactions of 3-oxy-4-pentenylmalonate derivatives proceeded with high cis-selectivity through stereoelectronic control of the oxygenated substituent at an allylic position. In the reaction of (S)-2-siloxy-4-pentenylmalonate, an excellent diastereoselectivity was achieved through the utilization of double stereodifferentiation with a chiral titanium catalyst. Furthermore, as an application of the present reaction, the asymmetric syntheses of cyclosarkomycin and a synthetic intermediate of brefeldin A from optically pure 2- and 3-oxy-4-pentenylmalonate derivatives are also described.

Original languageEnglish
Pages (from-to)8256-8263
Number of pages8
JournalJournal of Organic Chemistry
Volume61
Issue number23
DOIs
Publication statusPublished - 1996 Nov 15

ASJC Scopus subject areas

  • Organic Chemistry

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