Dual in Situ Generation of Aliphatic Vinyl Ethers and Electron-Deficient ortho-Quinone Methides for Inverse-Electron-Demand [4+2] Cycloaddition: A Selective One-Pot Synthesis of 3-Alkylchromanes

Kenta Tanaka, Ko Ueno, Yuta Tanaka, Naoya Ohtsuka, Yosuke Asada, Mami Kishimoto, Shuto Sunaga, Yujiro Hoshino, Kiyoshi Honda

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

An inverse-electron-demand [4+2] cycloaddition of in situ generated aliphatic vinyl ethers and electron-deficient ortho-quinone methides (o-QMs) has been developed. The reaction of in situ generated aliphatic vinyl ethers with o-QMs afforded the corresponding 3-alkylchromanes with high stereo- A nd regioselectivities. The method provides a versatile access to functionalized 3-alkylchromanes and it constitutes a useful tool for the synthesis of biologically active chromanes.

Original languageEnglish
Pages (from-to)1197-1200
Number of pages4
JournalSynlett
Volume31
Issue number12
DOIs
Publication statusPublished - Jul 22 2020
Externally publishedYes

Keywords

  • Catalysis
  • chromanes
  • ortho-quinone methides
  • salicylaldehydes
  • vinyl ethers
  • [4+2] cycloaddition

ASJC Scopus subject areas

  • Organic Chemistry

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