Asymmetric cycloadditions of palladium-polarized aza-o-xylylenes.
Vinyl benzoxazinanones undergo highly enantioselective decarboxylative cycloadditions with electron-deficient olefins in the presence of palladium catalysts. Palladium induces the decarboxylation of the parent benzoxazinanones under mild conditions to produce an intermediate that can be described as a polarized aza-o-xylylene. These intermediates undergo a formal [4 + 2] cycloaddition with good Michael acceptors to produce highly substituted hydroquinolines with excellent regio-, diastereo-, and enantioselectivities.
Department of Chemistry, University of Kansas, 2010 Malott Hall, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, USA.
Chao
C
Wang
Jon A
JA
Tunge
D001372:Aza Compounds; D010165:Palladium; D011804:Quinolines / Q000138:chemical synthesis*; D014992:Xylenes
D001372:Aza Compounds; D011804:Quinolines; D014992:Xylenes; D010165:Palladium