title: Dual Catalytic Decarboxylative Allylations of α-Amino Acids and Their Divergent Mechanisms.
abstract: The room temperature radical decarboxylative allylation of N-protected α-amino acids and esters has been accomplished via a combination of palladium and photoredox catalysis to provide homoallylic amines. Mechanistic investigations revealed that the stability of the α-amino radical, which is formed by decarboxylation, dictates the predominant reaction pathway between competing mechanisms.
authors.affiliation: Department of Chemistry, The University of Kansas, 2010 Malott Hall, 1251 Wescoe Hall Drive, Lawrence KS 66045 (USA).
authors.forename: Simon B
authors.initials: SB
authors.lastname: Lang
authors.affiliation: Department of Chemistry, The University of Kansas, 2010 Malott Hall, 1251 Wescoe Hall Drive, Lawrence KS 66045 (USA).
authors.forename: Kathryn M
authors.initials: KM
authors.lastname: O'Nele
authors.affiliation: Department of Chemistry, The University of Kansas, 2010 Malott Hall, 1251 Wescoe Hall Drive, Lawrence KS 66045 (USA).
authors.forename: Justin T
authors.initials: JT
authors.lastname: Douglas
authors.affiliation: Department of Chemistry, The University of Kansas, 2010 Malott Hall, 1251 Wescoe Hall Drive, Lawrence KS 66045 (USA). tunge@ku.edu.
authors.forename: Jon A
authors.initials: JA
authors.lastname: Tunge
mesh_terms: D000588:Amines / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D003653:Decarboxylation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry; D055668:Photochemical Processes
chemical_list: D000588:Amines; D000596:Amino Acids; D002264:Carboxylic Acids; D010165:Palladium
keywords: allylation; amino acids; cross-coupling; homogeneous catalysis; photocatalysis