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Enantioselective annulations for dihydroquinolones by in situ generation of azolium enolates.

ABSTRACT: A convergent, catalytic asymmetric formal [4 + 2] annulation for the synthesis of dihydroquinolones has been developed. Carboxylic acids can be employed as precursors to NHC enolates through an in situ activation strategy. Simultaneous generation of a reactive aza-o-quinone methide under the basic conditions employed for NHC generation leads to a dual activation approach.

SUBMITTER: Lee A

PROVIDER: S-EPMC4120988 | biostudies-literature | 2014 Jul

REPOSITORIES: biostudies-literature

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Enantioselective annulations for dihydroquinolones by in situ generation of azolium enolates.

Lee Anna A Younai Ashkaan A Price Christopher K CK Izquierdo Javier J Mishra Rama K RK Scheidt Karl A KA

Journal of the American Chemical Society 20140715 30

A convergent, catalytic asymmetric formal [4 + 2] annulation for the synthesis of dihydroquinolones has been developed. Carboxylic acids can be employed as precursors to NHC enolates through an in situ activation strategy. Simultaneous generation of a reactive aza-o-quinone methide under the basic conditions employed for NHC generation leads to a dual activation approach. ...[more]

PMID: 25017004

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