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

Tadashi Inoue, Osamu Kitagawa, Yoko Oda, Takeo Taguchi

研究成果: Article査読

25 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)8256-8263
ページ数8
ジャーナルJournal of Organic Chemistry
61
23
DOI
出版ステータスPublished - 1996 11 15
外部発表はい

ASJC Scopus subject areas

  • 有機化学

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