Cyclization reaction of cyano-substituted unsaturated esters prompted by conjugate addition of organoborons

Tomoya Miura, Tatsuro Harumashi, Masahiro Murakami

Research output: Contribution to journalArticlepeer-review

35 Citations (Scopus)

Abstract

(Chemical Equation Presented) Unsaturated esters possessing a pendent cyano moiety react with B-Ar-9-BBNs in the presence of a rhodium(I) catalyst to give the five- and six-membered β-enamino esters in good yield. An (oxa-π-allyl)rhodium(I) intermediate, formed by initial conjugate addition of an Ar-rhodium(I) species, undergoes a facile intramolecular addition to the cyano group to construct the carbocyclic skeletons.

Original languageEnglish
Pages (from-to)741-743
Number of pages3
JournalOrganic Letters
Volume9
Issue number5
DOIs
Publication statusPublished - Mar 1 2007
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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