An Expeditious Route to trans-Configured Tetrahydrothiophenes Enabled by Fe(OTf)3-Catalyzed [3+2] Cycloaddition of Donor–Acceptor Cyclopropanes with Thionoesters

Yohei Matsumoto, Daiki Nakatake, Ryo Yazaki, Takashi Ohshima

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

A synthetic route to trans-configured tetrahydrothiophenes (THTs) through Fe(OTf)3-promoted [3+2] cycloaddition of donor–acceptor cyclopropanes with thionoesters was developed. The cycloaddition proceeded in high yield with high diastereoselectivity, affording transient α-alkoxy THTs. Not only aromatic and aliphatic thionoesters, but also thionolactone were applicable to the present iron catalysis. Further transformation of the S,O-ketal functionality of the product was achieved in a highly trans diastereoselective manner. Moreover, the utility of our methodology was clearly demonstrated by the synthesis of enantioenriched trans-configured THTs.

Original languageEnglish
Pages (from-to)6062-6066
Number of pages5
JournalChemistry - A European Journal
Volume24
Issue number23
DOIs
Publication statusPublished - Apr 20 2018

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All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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