title: Phosphine-catalyzed regiospecific allylic amination and dynamic kinetic resolution of Morita-Baylis-Hillman acetates.
abstract: Exposure of Morita-Baylis-Hillman (MBH) acetates to tertiary phosphine catalysts in the presence of 4,5-dichlorophthalimide enables regiospecific allylic substitution through a tandem S(N)2'-S(N)2' mechanism. Through the use of the chiral phosphine catalyst (R)-Cl-MeO-BIPHEP, chiral racemic MBH acetate 4 is converted to the corresponding allylic amination product in 80% yield and 56% enantiomeric excess, thus establishing the feasibility of dynamic kinetic resolution. [reaction: see text]
authors.affiliation: Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, TX 78712, USA.
authors.forename: Chang-Woo
authors.initials: CW
authors.lastname: Cho
authors.forename: Jong-Rock
authors.initials: JR
authors.lastname: Kong
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Krische
mesh_terms: D000085:Acetates / Q000737:chemistry*; D000478:Alkylation; D000498:Allyl Compounds / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D007700:Kinetics; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000085:Acetates; D000498:Allyl Compounds; D010720:Phosphines; C044646:phosphine