Decarboxylative Intramolecular Cyclization and Sequential Halogenation of Cyclic Enol Carbonates ®Synthesis of Stereochemically-defined Seven-membered Carbocycles®

Haruki Yokoyama, Natsuki Kimaru, Akane Kozuma, Keiichi Komatsuki, Tohru Yamada, Kodai Saito

Research output: Contribution to journalArticlepeer-review

Abstract

The intramolecular cyclization for the construction of 7-membered carbocycles triggered by the decarboxylation of a cyclic enol carbonate was studied. In this study, it was found that the treatment of the alkene-tethered cyclic enol carbonate with a metal halide resulted in the decarboxylation and sequential intramolecular cyclization, followed by halogenation to give a functionalized 7-membered ketone with high stereoselectivity. Among the Lewis acidic metal halides, titanium tetrachloride was the most effective for this transformation. This method was applicable for a variety of substrates.

Original languageEnglish
Pages (from-to)867-869
Number of pages3
JournalChemistry Letters
Volume51
Issue number8
DOIs
Publication statusPublished - 2022 Aug

Keywords

  • Cyclization
  • Decarboxylation
  • Seven-membered ring

ASJC Scopus subject areas

  • Chemistry(all)

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