An asymmetric hetero-claisen approach to 3-alkyl-3-aryloxindoles.
The reaction of a chiral N-phenylnitrone derived from Garner's aldehyde with alkylarylketenes generates 3-alkyl-3-aryloxindoles directly in excellent yields and with good to excellent levels of enantioselectivity (up to 90% ee).
Duguet
Nicolas
N
EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, UK.
Slawin
Alexandra M Z
AM
Smith
Andrew D
AD
D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D000475:Alkenes; D007211:Indoles; D009589:Nitrogen Oxides; C015388:nitrones