Stereospecific cross-coupling of secondary alkyl β-trifluoroboratoamides

J Am Chem Soc. 2010 Dec 8;132(48):17108-10. doi: 10.1021/ja108949w. Epub 2010 Nov 15.

Abstract

The stereospecific cross-coupling of enantioenriched nonbenzylic secondary alkyl boron compounds has been achieved. The high selectivity toward product formation over an undesired β-H elimination pathway is achieved via an intramolecular coordination of an ancillary carbonyl to the metal center in the diorganopalladium intermediate.

Publication types

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

MeSH terms

  • Amides / chemistry*
  • Boron Compounds / chemistry*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Amides
  • Boron Compounds