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Asymmetric Cycloadditions of Palladium-Polarized Aza- o -xylylenes

2008; American Chemical Society; Volume: 130; Issue: 26 Linguagem: Inglês

10.1021/ja801742h

1943-2984

Chao Wang, Jon A. Tunge,

Asymmetric Synthesis and Catalysis

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.