Access to Electron-Deficient 2,2-Disubstituted Chromanes: A Highly Regioselective One-Pot Synthesis via an Inverse-Electron-Demand [4 + 2] Cycloaddition of ortho-Quinone Methides

Kenta Tanaka, Mami Kishimoto, Yosuke Asada, Yuta Tanaka, Yujiro Hoshino, Kiyoshi Honda

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

We report the one-pot synthesis of 2,2-disubstituted chromanes with electron-withdrawing substituents. This reaction provides a simple yet efficient route to a wide range of electron-deficient chromanes in high yield and excellent regioselectivity. The reaction of salicylaldehyde with 1,1-disubstituted ethylenes smoothly furnishes these electron-deficient chromanes, which can be further transformed into functionalized chromanes or chromene. For example, BW683C was effectively synthesized from 5-chlorosalicylaldehyde with 4-chlorostyrene in two steps in excellent yield. The present reaction thus provides versatile access to functionalized electron-deficient chromanes and chromenes and therefore constitutes a promising tool for the synthesis of biologically and photochemically active molecules.

Original languageEnglish
Pages (from-to)13858-13870
Number of pages13
JournalJournal of Organic Chemistry
Volume84
Issue number21
DOIs
Publication statusPublished - Nov 1 2019
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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