Fluoride-Mediated Dephosphonylation of α-Diazo-β-carbonyl Phosphonates

Ravindra S. Phatake, Venkannababu Mullapudi, Vivek C. Wakchaure, Chepuri V. Ramana

Research output: Contribution to journalArticlepeer-review

28 Scopus citations

Abstract

The possibility of fluoride-mediated selective dephosphonylation of α-diazo-β-carbonyl phosphonates such as the Ohira-Bestmann reagent has been proposed and executed. The resulting α-diazocarbonyl intermediates undergo a (3 + 2)-cycloaddition at room temperature with conjugated olefins and benzynes. Interestingly, under the current conditions, the resulting cycloaddition products underwent either N-acylation (with excess α-diazo-β-carbonyl phosphonates) or Michael addition (with conjugated olefins).

Original languageEnglish
Pages (from-to)372-375
Number of pages4
JournalOrganic Letters
Volume19
Issue number2
DOIs
StatePublished - 20 Jan 2017
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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