title: Beta-amino alcohol derived beta-hydroxy- and beta-(o-diphenylphosphino)benzoyloxy(o-diphenylphosphino)benzamides: an ester-amide ligand structural model for the palladium-catalyzed allylic alkylation reaction.
abstract: A commercially available collection of beta-amino alcohols have been converted to their corresponding beta-hydroxy- and beta-(o-diphenylphosphino)benzoyloxy(o-diphenylphosphino)benzamides 11a-f and 12a-f and have been employed in the Tsuji-Trost asymmetric alkylation reaction with 1,3-diphenylpropenyl acetate. With the exception of ligands 11b and 11f, the beta-hydroxybenzoyloxy(o-diphenylphosphino)benzamide ligands 11a-f primarily afforded the (R)-enantiomer of the product. In contrast, the bis(phosphine) ligands 12a-f consistently afforded the (S)-enantiomer. The best ligand (12c) was derived from cis-(1R,2S)-2-amino-1,2-diphenyl-1-ethanol, and when applied in the asymmetric allylic alkylation reaction, it yielded the product in an enantiomeric ratio of 97.8.22 favoring the (S)-enantiomer. A computational study was conducted on the conformation that this ligand might adopt in the palladium-catalyzed alkylation reaction as compared to that of the Trost ligand 1a.
authors.affiliation: Department of Chemistry, Illinois State University, Normal, Illinois 61790-4160, USA.
authors.forename: Geetanjali S
authors.initials: GS
authors.lastname: Mahadik
authors.forename: Stanley A
authors.initials: SA
authors.lastname: Knott
authors.forename: Lisa F
authors.initials: LF
authors.lastname: Szczepura
authors.forename: Steven J
authors.initials: SJ
authors.lastname: Peters
authors.forename: Jean M
authors.initials: JM
authors.lastname: Standard
authors.forename: Shawn R
authors.initials: SR
authors.lastname: Hitchcock