Chiral P,N-ligands based on ketopinic acid in the asymmetric Heck reaction.
[figure: see text] Novel chiral P,N-ligands were synthesized from (1S)-(+)-ketopinic acid using palladium-catalyzed coupling reaction of a vinyl triflate and either a diarylphosphine or a dialkylphosphine as the key step. Palladium complexes of these ligands are efficient catalysts for asymmetric Heck reaction between aryl or alkenyl triflates and cyclic alkenes. Products were obtained with good to excellent enantioselectivity from arylation and alkenylation of 1,2-dihydrofuran, cyclopentene, and 4,7-dihydro-1,3-dioxepin.
Gilbertson
S R
SR
Department of Chemistry, Washington University, One Brookings Drive, Campus Box 1134, St. Louis, Missouri 63130, USA. srg@wuchem.wustl.edu
Fu
Z
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D000475:Alkenes / Q000737:chemistry; D001952:Bridged-Ring Compounds; D002625:Chemistry, Organic / Q000379:methods; D007659:Ketones; D008024:Ligands; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium; D010720:Phosphines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000475:Alkenes; D001952:Bridged-Ring Compounds; D007659:Ketones; D008024:Ligands; D010080:Oxazoles; D010720:Phosphines; C431983:ketopinic acid; D010165:Palladium