title: Pd-Catalyzed Acyl C-O Bond Activation for Selective Ring-Opening of α-Methylene-β-lactones with Amines.
abstract: A Pd-catalyzed ring-opening of β-lactones with various types of amines (primary, secondary, and aryl) to provide β-hydroxy amides with excellent selectivity toward acyl C-O bond cleavage is reported. The utility of this protocol is demonstrated in an asymmetric kinetic resolution providing enantioenriched α-methylene-β-lactones.
authors.affiliation: Department of Chemistry, University of Connecticut , Storrs, Connecticut 06269-3060, United States.
authors.forename: Christian A
authors.initials: CA
authors.lastname: Malapit
authors.affiliation: Department of Chemistry, University of Connecticut , Storrs, Connecticut 06269-3060, United States.
authors.forename: Donald R
authors.initials: DR
authors.lastname: Caldwell
authors.affiliation: Department of Chemistry, University of Connecticut , Storrs, Connecticut 06269-3060, United States.
authors.forename: Nicole
authors.initials: N
authors.lastname: Sassu
authors.affiliation: Department of Chemistry, University of Connecticut , Storrs, Connecticut 06269-3060, United States.
authors.forename: Samuel
authors.initials: S
authors.lastname: Milbin
authors.affiliation: Department of Chemistry, University of Connecticut , Storrs, Connecticut 06269-3060, United States.
authors.forename: Amy R
authors.identifier: 0000-0003-1958-6411
authors.initials: AR
authors.lastname: Howell
mesh_terms: D000577:Amides / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D007700:Kinetics; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000577:Amides; D000588:Amines; D007783:Lactones; C416683:methylene-lactone; D010165:Palladium