(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

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)5696-5703
Number of pages8
JournalJournal of Organic Chemistry
Volume80
Issue number11
DOIs
Publication statusPublished - Jun 5 2015
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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