title: Efficient synthesis of chiral beta-seleno amides via ring-opening reaction of 2-oxazolines and their application in the palladium-catalyzed asymmetric allylic alkylation.
abstract: [structure: see text] A set of chiral beta-seleno amides have been efficiently synthesized via the ring-opening reaction of chiral 2-oxazolines by selenium nucleophiles. The present method is applicable to the synthesis of beta-seleno amides containing thioether, alcohol, and ether moieties in good yields. As an application, the synthesis of a selenocysteine derivative has been accomplished. Additionally, these new compounds were evaluated in the palladium-catalyzed asymmetric allylic alkylation, giving the alkylated products in up to 98% ee.
authors.affiliation: Departamento de Química, Universidade Federal de Santa Maria, RS, Brazil. albraga@quimica.ufsm.br
authors.forename: Antonio L
authors.initials: AL
authors.lastname: Braga
authors.forename: Fabrício
authors.initials: F
authors.lastname: Vargas
authors.forename: Jasquer A
authors.initials: JA
authors.lastname: Sehnem
authors.forename: Rodolpho C
authors.initials: RC
authors.lastname: Braga
mesh_terms: D000478:Alkylation; D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010081:Oxazolone / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D012643:Selenium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000577:Amides; D010081:Oxazolone; D010165:Palladium; D012643:Selenium