title: Design, synthesis, and applications of potential substitutes of t-Bu-phosphinooxazoline in Pd-catalyzed asymmetric transformations and their use for the improvement of the enantioselectivity in the Pd-catalyzed allylation reaction of fluorinated allyl enol carbonates.
abstract: The design, synthesis, and applications of potential substitutes of t-Bu-PHOX in asymmetric catalysis is reported. The design relies on the incorporation of geminal substituents at C5 in combination with a substituent at C4 other than t-butyl (i-Pr, i-Bu, or s-Bu). Most of these new members of the PHOX ligand family behave similarly in terms of stereoinduction to t-Bu-PHOX in three palladium-catalyzed asymmetric transformations. Electronically modified ligands were also prepared and used to improve the enantioselectivity in the Pd-catalyzed allylation reaction of fluorinated allyl enol carbonates.
authors.affiliation: Département de chimie, Université Laval, 1045 avenue de la Médecine, Québec, QC, Canada G1V 0A6.
authors.forename: Étienne
authors.initials: É
authors.lastname: Bélanger
authors.forename: Marie-France
authors.initials: MF
authors.lastname: Pouliot
authors.forename: Marc-André
authors.initials: MA
authors.lastname: Courtemanche
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Paquin
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000498:Allyl Compounds / Q000737:chemistry*; D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D054879:Halogenation; D008024:Ligands; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D010720:Phosphines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000498:Allyl Compounds; D002254:Carbonates; D008024:Ligands; D010080:Oxazoles; D010720:Phosphines; C572515:t-Bu-phosphinooxazoline; D010165:Palladium