New Silicon-Phosphorus Reagents in Organic Synthesis. Carbonyl and Conjugate Addition Reactions of Silicon Phosphite Esters and Related Systems

David A. Evans, Kenneth M. Hurst, James M. Takacs

Research output: Contribution to journalArticle

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Abstract

The 1,2- and 1,4-addition reactions of organosilicon tervalent phosphorus esters, X2POSiR3 (X = OMe, NMe2, Ph), with saturated and α,β-unsaturated aldehydes and ketones have been studied. These addition reactions have been compared with the complementary reactions of alkyl phosphorus esters, X2POCH3, and R3SiCl with carbonyl substrates. With α,β-unsaturated aldehydes, a judicious choice of reagent and conditions leads to the regioselective 1,2- or 1,4-addition mode. Some of the mechanistic details of these addition reactions have been elucidated.

Original languageEnglish (US)
Pages (from-to)3467-3477
Number of pages11
JournalJournal of the American Chemical Society
Volume100
Issue number11
DOIs
Publication statusPublished - Jan 1 1978

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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