[1,2]-Wittig rearrangement of acetal systems: A highly stereocontrolled conversion of O-glycosides to C-glycosides

K. Tomooka, H. Yamamoto, T. Nakai

研究成果: Contribution to journalArticle査読

67 被引用数 (Scopus)

抄録

We envisioned that acetal systems such as O-glycosides would undergo the [1,2]-Wittig shift with great facility owing to the relatively large stability of the α-oxy radical, together with retention of the anomeric configuration. We now wish to report that the [1,2]-Wittig rearrangement of O-glycosides proceeds with efficient stereocontrol over both the anomeric center and the new chiral center formed on the side chain to give the stereo-defined C-glycosides in high yields. We have demonstrated that the [1,2]-Wittig rearrangement of O-glycosides proceeds with efficient stereocontrol over both the anomeric center and the side-chain chiral center to give a novel class of the stereo-defined C-glycosides which is otherwise difficult to obtain.

本文言語英語
ページ(範囲)3317-3318
ページ数2
ジャーナルJournal of the American Chemical Society
118
13
DOI
出版ステータス出版済み - 4 3 1996
外部発表はい

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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