Research on unique masked ortho-benzoquinone, monohemiaminal: Synthesis and reactions

Yuri Matsumoto, Akihiko Nakamura, Emi Saito, Masahisa Nakada

Research output: Contribution to journalArticle

Abstract

Synthesis of ortho-benzoquinone monohemiaminals via the oxidative dearomatization/O-cyclization cascades of phenols bearing an ortho substituent derived from an amino alcohol with PIDA is described. The cascade reactions of substrates bearing a chiral substituent were found to proceed in a stereoselective manner. The Diels-Alder reactions of the ortho-benzoquinone monohemiaminals proceed in a highly stereoselective manner. The oxidative dearomatization/O-cyclization cascade affording the ortho-benzoquinone monohemiaminal had never been reported; hence, there is still ample scope for further investigation.

Original languageEnglish
Pages (from-to)232-252
Number of pages21
JournalHeterocycles
Volume97
Issue number1
DOIs
Publication statusPublished - 2018 Jan 1

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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