Intramolecular Consecutive Dehydro-Diels–Alder Reaction for the Catalytic and Enantioselective Construction of Axial Chirality

Takanori Shibata, Ayato Sekine, Akihito Mitake, Stephen Kyalo Kanyiva

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Consecutive thermal and metal-catalyzed dehydro-Diels–Alder (DDA) reactions of sulfur-tethered tetraynes, possessing a 1,3-diyne moiety, proceeded efficiently, and axial chirality was achieved for the resulting dibenzothiophenyl moieties. Chiral-rhodium catalysis realized a highly enantioselective synthesis, and transformations into bis(benzocarbazole) derivatives were also achieved.

Original languageEnglish
JournalAngewandte Chemie - International Edition
DOIs
Publication statusAccepted/In press - 2018 Jan 1

Fingerprint

Rhodium
Chirality
Sulfur
Catalysis
Metals
Derivatives
Hot Temperature

Keywords

  • axial chirality
  • cycloaddition
  • enantioselectivity
  • heterocycles
  • rhodium

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

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AB - Consecutive thermal and metal-catalyzed dehydro-Diels–Alder (DDA) reactions of sulfur-tethered tetraynes, possessing a 1,3-diyne moiety, proceeded efficiently, and axial chirality was achieved for the resulting dibenzothiophenyl moieties. Chiral-rhodium catalysis realized a highly enantioselective synthesis, and transformations into bis(benzocarbazole) derivatives were also achieved.

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KW - heterocycles

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