Enantioselective Synthesis of Sulfur-Containing Medium-Ring Heterocycles with Axial Chiralities by Catalytic Intramolecular [2+2+2] Cycloaddition

Akihito Mitake, Toru Fusamae, Stephen Kyalo Kanyiva, Takanori Shibata

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The rhodium-catalyzed enantioselective intramolecular cycloaddition of triynes connected by sulfur-containing tethers gave tribenzothiepins and a tribenzodithiocin in high yields with good-to-excellent enantiomeric excesses. The present protocol generated axial chiralities fused with medium-ring heterocycles. In particular, this is the first example of the catalytic and highly enantioselective construction of a tribenzodiheterocin skeleton.

Original languageEnglish
Pages (from-to)7266-7270
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2017
Issue number48
DOIs
Publication statusPublished - 2017 Dec 29

Fingerprint

Rhodium
Cycloaddition
Chirality
cycloaddition
rhodium
musculoskeletal system
chirality
Sulfur
sulfur
rings
synthesis

Keywords

  • Alkynes
  • Axial chirality
  • Cycloaddition
  • Enantioselectivity
  • Heterocycles
  • Rhodium

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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abstract = "The rhodium-catalyzed enantioselective intramolecular cycloaddition of triynes connected by sulfur-containing tethers gave tribenzothiepins and a tribenzodithiocin in high yields with good-to-excellent enantiomeric excesses. The present protocol generated axial chiralities fused with medium-ring heterocycles. In particular, this is the first example of the catalytic and highly enantioselective construction of a tribenzodiheterocin skeleton.",
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author = "Akihito Mitake and Toru Fusamae and Kanyiva, {Stephen Kyalo} and Takanori Shibata",
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T1 - Enantioselective Synthesis of Sulfur-Containing Medium-Ring Heterocycles with Axial Chiralities by Catalytic Intramolecular [2+2+2] Cycloaddition

AU - Mitake, Akihito

AU - Fusamae, Toru

AU - Kanyiva, Stephen Kyalo

AU - Shibata, Takanori

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AB - The rhodium-catalyzed enantioselective intramolecular cycloaddition of triynes connected by sulfur-containing tethers gave tribenzothiepins and a tribenzodithiocin in high yields with good-to-excellent enantiomeric excesses. The present protocol generated axial chiralities fused with medium-ring heterocycles. In particular, this is the first example of the catalytic and highly enantioselective construction of a tribenzodiheterocin skeleton.

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KW - Heterocycles

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