Asymmetric Synthesis of a 5,7-Fused Ring System Enabled by an Intramolecular Buchner Reaction with Chiral Rhodium Catalyst

Takayuki Hoshi, Eisuke Ota, Yasuhide Inokuma, Junichiro Yamaguchi

Research output: Contribution to journalArticle

Abstract

A Rh-catalyzed asymmetric intramolecular Buchner ring expansion of α-alkyl-α-diazoesters has been developed. The present protocol generates a 5,7-fused ring system in an enantioselective manner while minimizing β-hydrogen migration, which has been a competing reaction when using α-alkyl-α-diazoesters. The ester functionality at the bridgehead position would be a useful synthetic handle for further derivatization to complex molecules including natural products.

Original languageEnglish
Pages (from-to)10081-10084
Number of pages4
JournalOrganic Letters
Volume21
Issue number24
DOIs
Publication statusPublished - 2019 Dec 20

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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