Enantioselective Synthesis of Nine- to Eleven-Membered Cyclic Polyphenylenes Containing Heteroatoms by Catalytic Intramolecular [2+2+2] Cycloaddition

Takanori Shibata, Toru Fusamae, Hideaki Takano, Natsuhiko Sugimura, Stephen Kyalo Kanyiva

Research output: Contribution to journalArticle

Abstract

Rh-catalyzed enantioselective intramolecular reactions of triynes consisting of 1,6-diyne and 1,10-diyne moieties tethered by sulfur or oxygen and ortho-phenylene moieties proceeded to give chiral tetrabenzoheteronines possessing a nine-membered ring system as [2+2+2] cycloadducts. In the reaction of triynes consisting of 1,6-diyne and 1,11-diyne moieties, sulfur-tethered substrates gave chiral metacyclophanes with an eleven-membered ring system, whereas an oxygen- and sulfur-tethered substrate afforded a tetrabenzo-1,4-oxathiecine with a ten-membered ring system. The mechanisms of the different reaction pathways depending on the heteroatom of the tether are discussed.

Original languageEnglish
JournalAsian Journal of Organic Chemistry
DOIs
Publication statusPublished - 2019 Jan 1

Keywords

  • axial chirality
  • cycloaddition
  • enantioselectivity
  • heterocycles
  • medium ring system

ASJC Scopus subject areas

  • Organic Chemistry

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