Palladium-catalyzed regio-, diastereo-, and enantioselective allylation of nitroalkanes with monosubstituted allylic substrates

J Org Chem. 2013 Jul 5;78(13):6503-9. doi: 10.1021/jo400663d. Epub 2013 Jun 24.

Abstract

Pd-catalyzed asymmetric allylic alkylation of nitroalkanes and monosubstituted allylic substrates was performed to afford products with two adjacent chiral centers and with excellent regio-, diastereo-, and enantioselectivities. The usefulness of the protocol in organic synthesis was demonstrated by transformation of the product to an optically active homoallylamine, a 2,3-disubstituted tetrahydropyridine, and an α,β-disubstituted amino acid derivative.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkanes / chemistry*
  • Allyl Compounds / chemistry*
  • Allylamine / chemical synthesis*
  • Allylamine / chemistry
  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Catalysis
  • Molecular Structure
  • Nitro Compounds / chemistry*
  • Organometallic Compounds / chemistry*
  • Palladium / chemistry
  • Stereoisomerism

Substances

  • Alkanes
  • Allyl Compounds
  • Amino Acids
  • Nitro Compounds
  • Organometallic Compounds
  • Allylamine
  • Palladium