Enantioselective Boronate Additions to N-Acyl Quinoliniums Catalyzed by Tartaric Acid

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...

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Bibliographic Details
Published inOrganic letters Vol. 13; no. 23; pp. 6316 - 6319
Main Authors Kodama, Tomohiro, Moquist, Philip N, Schaus, Scott E
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.12.2011
Amer Chemical Soc
Subjects
Acetals - chemistry
Boronic Acids - chemistry
Catalysis
Chemistry
Chemistry, Organic
Combinatorial Chemistry Techniques
Molecular Structure
Physical Sciences
Quinolines - chemical synthesis
Quinolines - chemistry
Science & Technology
Stereoisomerism
Tartrates - chemistry
SYSTEM
ENONES
BORATE
CONVENIENT REAGENT
ESTERS
RESOLUTION
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Summary: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.
Bibliography:NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol2028702