Stereoselective vinylation of aryl N-(2-pyridylsulfonyl) aldimines with 1-alkenyl-1,1-heterobimetallic reagents

Org Lett. 2011 Dec 16;13(24):6464-7. doi: 10.1021/ol202766g. Epub 2011 Nov 15.

Abstract

Vinylation of aryl N-(2-pyridylsulfonyl) aldimines with versatile 1-alkenyl-1,1-borozinc heterobimetallic reagents is disclosed. In situ hydroboration of air-stable B(pin)-alkynes followed by chemoselective transmetalation with dimethylzinc and addition to aldimines provides B(pin)-substituted allylic amines in 53-93% yield in a one-pot procedure. The addition step can be followed by either B-C bond oxidation to provide α-amino ketones (71-98% yield) or Suzuki cross-coupling to furnish trisubstituted 2-arylated (E)-allylic amines (51-73% yield).

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

  • Alkenes / chemistry*
  • Alkynes / chemistry
  • Combinatorial Chemistry Techniques
  • Imines / chemistry*
  • Indicators and Reagents
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Pyridines / chemistry*
  • Stereoisomerism
  • Sulfones / chemistry*
  • Zinc / chemistry

Substances

  • Alkenes
  • Alkynes
  • Imines
  • Indicators and Reagents
  • Organometallic Compounds
  • Pyridines
  • Sulfones
  • Zinc