Si-based benzylic 1,4-rearrangement/cyclization reaction

Org Lett. 2009 Feb 5;11(3):511-3. doi: 10.1021/ol802289f.

Abstract

The trans-selective hydrosilylation of ynones (1) yields beta-silylated enones (2) that undergo a benzylic 1,4-rearrangement/cyclization reaction in the presence of base, yielding 2,5-dihydro-1,2-oxasiloles (3).

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkynes / chemistry*
  • Benzene Derivatives / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Cyclization
  • Ketones / chemistry*
  • Molecular Structure
  • Organosilicon Compounds / chemical synthesis*
  • Organosilicon Compounds / chemistry*
  • Stereoisomerism

Substances

  • Alkynes
  • Benzene Derivatives
  • Ketones
  • Organosilicon Compounds