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Enantioselective boronate additions to N-acyl quinoliniums catalyzed by tartaric acid.

ABSTRACT: Tartaric acid catalyzes the asymmetric addition of vinylboronates to N-acyl quinoliniums, affording highly enantioenriched dihydroquinolines. The catalyst serves to activate the boronate through a ligand-exchange reaction and generates the N-acyl quinolinium in situ from the stable quinoline-derived N,O-acetal.

SUBMITTER: Kodama T 

PROVIDER: S-EPMC4655815 | biostudies-literature | 2011 Dec

REPOSITORIES: biostudies-literature

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Enantioselective boronate additions to N-acyl quinoliniums catalyzed by tartaric acid.

Kodama Tomohiro T   Moquist Philip N PN   Schaus Scott E SE  

Organic letters 20111108 23

Tartaric acid catalyzes the asymmetric addition of vinylboronates to N-acyl quinoliniums, affording highly enantioenriched dihydroquinolines. The catalyst serves to activate the boronate through a ligand-exchange reaction and generates the N-acyl quinolinium in situ from the stable quinoline-derived N,O-acetal. ...[more]

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