Enantioselective hydrogenation of 3-alkylidenelactams: high-throughput screening provides a surprising solution

J Am Chem Soc. 2002 Nov 20;124(46):13692-3. doi: 10.1021/ja028043y.

Abstract

High-throughput screening of 256 potential catalysts (8 metal precursors x 32 phosphine ligands) has identified [(BDPP)Ir(COD)]BF4 as a catalyst for the enantioselective hydrogenation of 3-alkylidenelactams. This result is surprising given the highly flexible backbone of the BDPP ligand and the ineffectiveness of this catalyst in other applications. The asymmetric hydrogenation appears fairly general for five- and six-membered lactams and in one case has been scaled up to a 20 kg level.

MeSH terms

  • Alkadienes / chemistry
  • Alkenes / chemistry*
  • Hydrogenation
  • Lactams / chemistry*
  • Pentanes / chemistry
  • Phosphines / chemistry
  • Stereoisomerism

Substances

  • 2,4-bis(diphenylphosphino)pentane
  • Alkadienes
  • Alkenes
  • Lactams
  • Pentanes
  • Phosphines
  • 1,5-cyclooctadiene