Highly Selective One-Pot Synthesis of Polysubstituted Isoflavanes using Styryl Ethers and Electron-Withdrawing ortho -Quinone Methides Generated in Situ

Kenta Tanaka, Mami Kishimoto, Naoya Ohtsuka, Yoshinori Iwama, Hiroki Wada, Yujiro Hoshino, Kiyoshi Honda

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

A highly selective one-pot synthesis of polysubstituted isoflavanes has been developed. The reaction proceeds through the cycloaddition of methyl styryl ethers, derived from phenylacetaldehyde dimethyl acetals under acidic conditions, with electron-withdrawing ortho -quinone methides generated in situ. When phenylacetaldehyde dimethyl acetals were reacted with salicylaldehydes, the reaction proceeded smoothly to afford the corresponding isoflavanes stereoselectively in high yields and with excellent regioselectivities. The present reaction provides versatile access to functionalized isoflavanes, and constitutes a useful tool for the synthesis of biologically active molecules.

Original languageEnglish
Pages (from-to)189-192
Number of pages4
JournalSynlett
Volume30
Issue number2
DOIs
Publication statusPublished - 2019
Externally publishedYes

Keywords

  • isoflavan
  • ortho -quinone methide
  • regioselective synthesis
  • stereoselective synthesis
  • [4+2] cycloaddition

ASJC Scopus subject areas

  • Organic Chemistry

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