High asymmetric induction with beta-turn-derived palladium phosphine complexes.
[reaction: see text] Work toward the development of a bisphosphine ligand system for the palladium-catalyzed addition to cyclic allyl acetates is reported. A parallel approach using phosphine-containing amino acids in conjunction with natural amino acids was used to develop a selective ligand system. The ligand system was examined while attached to the polymer support as well as in solution. Selectivites with the difficult substrate 3-acetoxycyclopentene of up to 95% ee are reported.
Greenfield
Scott J
SJ
Department of Chemistry, Washington University, One Brookings Drive, Campus 1134, Saint Louis, Missouri 63130-4899, USA.
Agarkov
Anton
A
Gilbertson
Scott R
SR
D000085:Acetates / Q000737:chemistry; D000595:Amino Acid Sequence; D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D003517:Cyclopentanes / Q000737:chemistry; D008024:Ligands; D008958:Models, Molecular; D009842:Oligopeptides / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D017433:Protein Structure, Secondary; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000085:Acetates; D000596:Amino Acids; D003517:Cyclopentanes; D008024:Ligands; D009842:Oligopeptides; D009942:Organometallic Compounds; D010720:Phosphines; D010165:Palladium