Enantio- and diastereoselective palladium catalysed arylative and vinylative allene carbocyclisation cascades

Chem Commun (Camb). 2013 Jun 11;49(46):5265-7. doi: 10.1039/c3cc42079e.

Abstract

The enantioselective synthesis of heavily decorated spirolactams has been accomplished via an arylative or vinylative allene carbocyclisation cascade. Mediated by silver phosphate, a range of allene-linked pro-nucleophiles and aryl or vinyl iodides were reacted in the presence of catalytic Pd(OAc)2 and chiral bis(oxazoline) ligands to afford the spirolactam products in good yields and high enantio- and diastereoselectivities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkadienes / chemical synthesis
  • Alkadienes / chemistry*
  • Catalysis
  • Lactams / chemical synthesis*
  • Lactams / chemistry
  • Palladium / chemistry*
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Stereoisomerism
  • Vinyl Compounds / chemical synthesis
  • Vinyl Compounds / chemistry

Substances

  • Alkadienes
  • Lactams
  • Spiro Compounds
  • Vinyl Compounds
  • vinyl iodide
  • propadiene
  • Palladium