Catalytic and Enantioselective Synthesis of Chiral Multisubstituted Tribenzothiepins by Intermolecular Cycloadditions

Yu Ki Tahara, Riku Matsubara, Akihito Mitake, Tatsuki Sato, Kyalo Stephen Kanyiva, Takanori Shibata

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

The first catalytic and highly enantioselective synthesis of tribenzothiepin derivatives was achieved. Two types of intermolecular cycloadditions using either diphenyl-sulfide-tethered diynes or 2-phenyl sulfanylbenzene-tethered diynes with a monoalkyne successfully gave chiral multisubstituted tribenzothiepins in good to excellent ee values under mild conditions. The inversion energy of this saddle-shaped molecule was calculated by measurement of the racemization rate of chiral tribenzothiepins using the Eyring kinetic equation under heating conditions. The present protocol could also be used to prepare a chiral tribenzoselenepin.

Original languageEnglish
Pages (from-to)4552-4556
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number14
DOIs
Publication statusPublished - 2016 Mar 24

Keywords

  • chirality
  • cycloaddition
  • enantioselectivity
  • rhodium
  • synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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