Amino acid-derived hydroxamic acids as chiral ligands in the vanadium catalysed epoxidation.
New sulfonamide-derived hydroxamic acids have been developed as chiral ligands for the V-catalysed asymmetric epoxidation, showing high reactivity at subzero temperatures and moderate to good enantioselectivity. The strong accelerating effect exhibited by the ligands of this type can be attributed to the sulfonamide functionality. A range of cinnamyl type allylic alcohols were epoxidised with up to 74% ee.
Malkov
Andrei V
AV
Department of Chemistry, WestChem, Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, Scotland, UK. amalkov@chem.gla.ac.uk
Bourhani
Zaïnaba
Z
Kocovský
Pavel
P
D000438:Alcohols / Q000737:chemistry; D002384:Catalysis; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D006877:Hydroxamic Acids / Q000737:chemistry*; D008024:Ligands; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*; D014639:Vanadium / Q000737:chemistry*
D000438:Alcohols; D004852:Epoxy Compounds; D006877:Hydroxamic Acids; D008024:Ligands; D009942:Organometallic Compounds; D013449:Sulfonamides; D014639:Vanadium