title: Enantioselective synthesis of dialkylated N-heterocycles by palladium-catalyzed allylic alkylation.
abstract: The enantioselective synthesis of α-disubstituted N-heterocyclic carbonyl compounds has been accomplished using palladium-catalyzed allylic alkylation. These catalytic conditions enable access to various heterocycles, such as morpholinone, thiomorpholinone, oxazolidin-4-one, 1,2-oxazepan-3-one, 1,3-oxazinan-4-one, and structurally related lactams, all bearing fully substituted α-positions. Broad functional group tolerance was explored at the α-position in the morpholinone series. We demonstrate the utility of this method by performing various transformations on our useful products to readily access a number of enantioenriched compounds.
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology , 1200 East California Boulevard, MC 101-20, Pasadena, California 91125, United States.
authors.forename: Yoshitaka
authors.initials: Y
authors.lastname: Numajiri
authors.forename: Gonzalo
authors.initials: G
authors.lastname: Jiménez-Osés
authors.forename: Bo
authors.initials: B
authors.lastname: Wang
authors.forename: K N
authors.initials: KN
authors.lastname: Houk
authors.forename: Brian M
authors.initials: BM
authors.lastname: Stoltz
mesh_terms: D000478:Alkylation; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006573:Heterocyclic Compounds, 1-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009025:Morpholines / Q000138:chemical synthesis / Q000737:chemistry; D010077:Oxazepines / Q000138:chemical synthesis / Q000737:chemistry; D023303:Oxazolidinones / Q000138:chemical synthesis / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D006573:Heterocyclic Compounds, 1-Ring; D007659:Ketones; D009025:Morpholines; D010077:Oxazepines; D023303:Oxazolidinones; D010165:Palladium