Improved dimethylzinc-promoted vinylation of nitrones with vinylboronic esters

Nageswaran Praveenganesh, Cristina De Candia, Antony Memboeuf, György Lendvay, Yves Gimbert, Pierre Y. Chavant

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Vinylboronic esters derived from 4,4,6-trimethyl-[1,3,2]dioxaborinane react with nitrones in the presence of dimethylzinc; nucleophilic addition of the vinyl group onto nitrones produces N-allylic hydroxylamines in fair yields. The sequence is compatible with various functional groups on the vinylic moiety. The mechanism and kinetic aspects are discussed on the basis of DFT calculations.

Original languageEnglish
Pages (from-to)2447-2454
Number of pages8
JournalJournal of Organometallic Chemistry
Volume695
Issue number22
DOIs
Publication statusPublished - Oct 15 2010

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Keywords

  • Allyl-hydroxylamines
  • Boron
  • Transmetallation
  • Vinylboronates
  • Zinc

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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