Acyl 1,3-migration in rhodium-catalyzed reactions of acetylenic β-ketoesters with aryl boronic acids: Application to two-carbon-atom ring expansions

Tomoya Miura, Masahiko Shimada, Masahiro Murakami

Research output: Contribution to journalArticlepeer-review

44 Citations (Scopus)

Abstract

(Chemical Equation Presented) Expanding rings: An intermediate organorhodium(I) species formed in the RhI-catalyzed reaction of acetylenic β-ketoesters and β-diketones with aryl boronic acids undergoes intramolecular nucleophilic addition to a ketone carbonyl group. The ensuing ring-opening reaction of the resulting cyclobutanols results in acyl 1,3-migration leading to the development of a two-carbon-atom ring-expansion reaction.

Original languageEnglish
Pages (from-to)7598-7600
Number of pages3
JournalAngewandte Chemie - International Edition
Volume44
Issue number46
DOIs
Publication statusPublished - Nov 25 2005
Externally publishedYes

Keywords

  • Acyl migration
  • Boron
  • Cyclizations
  • Rhodium
  • Ring expansion

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Fingerprint

Dive into the research topics of 'Acyl 1,3-migration in rhodium-catalyzed reactions of acetylenic β-ketoesters with aryl boronic acids: Application to two-carbon-atom ring expansions'. Together they form a unique fingerprint.

Cite this