Regioselective and Enantioselective Hydroformylation of Dialkylacrylamides

Gary M. Noonan, David Newton, Christopher J. Cobley, Andres Suarez, Antonio Pizzano, Matt Clarke

Research output: Contribution to journalArticlepeer-review

34 Citations (Scopus)

Abstract

Dimethylacrylamide can be hydroformylated with very high chemo- and regioselectivity. Asymmetric hydroformylation of this substrate is possible, provided steps are taken to minimise racemisation of the aldehyde products, and this work demonstrates the effect of various conditions and variables on racemisation. Using the Landis diazaphospholane ligands up to 68% ee can be realised under very mild conditions. Other dialkylacrylamides were also hydroformylated under mild conditions giving similar or better enantioselectivities, including the Weinreb amide of acrylic acid (71% ee), and the asymmetric hydroformylation of diethylacrylamide producing the chiral aldehyde with up to 82% ee.

Original languageEnglish
Pages (from-to)1047-1054
Number of pages8
JournalAdvanced Synthesis & Catalysis
Volume352
Issue number6
DOIs
Publication statusPublished - Apr 2010

Keywords

  • aldehydes
  • asymmetric carbonylation
  • hydroaminomethylation
  • hydroformylation
  • racemization
  • RHODIUM-CATALYZED HYDROFORMYLATION
  • PHOSPHINE-PHOSPHITE LIGANDS
  • ASYMMETRIC HYDROFORMYLATION
  • RH-CATALYSTS
  • SEQUENTIAL HYDROFORMYLATION
  • UNSATURATED ESTERS
  • METAL-CATALYSIS
  • TANDEM METAL
  • OLEFINS
  • COMPLEXES

Fingerprint

Dive into the research topics of 'Regioselective and Enantioselective Hydroformylation of Dialkylacrylamides'. Together they form a unique fingerprint.

Cite this