Efficient synthesis of chiral beta-seleno amides via ring-opening reaction of 2-oxazolines and their application in the palladium-catalyzed asymmetric allylic alkylation.
[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.
Braga
Antonio L
AL
Departamento de Química, Universidade Federal de Santa Maria, RS, Brazil. albraga@quimica.ufsm.br
Vargas
Fabrício
F
Sehnem
Jasquer A
JA
Braga
Rodolpho C
RC
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
D000577:Amides; D010081:Oxazolone; D010165:Palladium; D012643:Selenium