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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Bearings (structural)
Cyclization
Research
Amino Alcohols
Phenols
Cycloaddition Reaction
Substrates
benzoquinone

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Cite this

Research on unique masked ortho-benzoquinone, monohemiaminal : Synthesis and reactions. / Matsumoto, Yuri; Nakamura, Akihiko; Saito, Emi; Nakada, Masahisa.

In: Heterocycles, Vol. 97, No. 1, 01.01.2018, p. 232-252.

Research output: Contribution to journalArticle

Matsumoto, Yuri ; Nakamura, Akihiko ; Saito, Emi ; Nakada, Masahisa. / Research on unique masked ortho-benzoquinone, monohemiaminal : Synthesis and reactions. In: Heterocycles. 2018 ; Vol. 97, No. 1. pp. 232-252.
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