(Z)-Selective enol triflation of α-alkoxyacetoaldehydes: Application to synthesis of (Z)-allylic alcohols via cross-coupling reaction and [1,2]-wittig rearrangement

Fumiya Kurosawa, Takeo Nakano, Takahiro Soeta, Kohei Endo, Yutaka Ukaji

研究成果: Contribution to journalArticle査読

9 被引用数 (Scopus)

抄録

The stereoselective transformation of α-alkoxyacetoaldehydes to the corresponding (Z)-vinyl triflates was achieved by treatment with phenyl triflimide and DBU. The stereochemistry was explained by the "syn-effect," which was attributed primarily to an σ → π∗ interaction. The β-alkoxy vinyl triflates obtained were applied to the stereoselective synthesis of structurally diverse (Z)-allylic alcohols via transition metal-catalyzed cross-coupling reaction and [1,2]-Wittig rearrangement.

本文言語英語
ページ(範囲)5696-5703
ページ数8
ジャーナルJournal of Organic Chemistry
80
11
DOI
出版ステータス出版済み - 6 5 2015
外部発表はい

All Science Journal Classification (ASJC) codes

  • 有機化学

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