Asymmetric Synthesis of Benzylic Quaternary Difunctionalized Carbons Mediated by a Remote Sulfinyl Group

Enantiomerically enriched α-aryl α-cyanoacetates and α-aryl α-acylacetonitriles bearing a benzylic quaternary stereocenter have been readily synthesized by stereoselective reaction of 2-alkyl-2-[2-(p-tolylsulfinyl)phenyl]acetonitriles with different acylating and alkoxycarbonylating reagents under b...

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Bibliographic Details
Published in:Journal of organic chemistry 2011-05, Vol.76 (9), p.3597-3603
Main Authors: García Ruano, José Luis, Torrente, Esther, Martín-Castro, Ana M
Format: Article
Language:English
Subjects:
Benzene - chemical synthesis
Benzene - chemistry
Carbon - chemistry
Chemistry
Exact sciences and technology
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Stereoisomerism
Substrate Specificity
Sulfoxides - chemistry
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Summary:Enantiomerically enriched α-aryl α-cyanoacetates and α-aryl α-acylacetonitriles bearing a benzylic quaternary stereocenter have been readily synthesized by stereoselective reaction of 2-alkyl-2-[2-(p-tolylsulfinyl)phenyl]acetonitriles with different acylating and alkoxycarbonylating reagents under basic conditions. The stereoselectivity of the reactions proved closely dependent on the nature of the intermediate carbanionic species, the evolution of which was effectively controlled by a sulfinyl group as a remote chiral auxiliary.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo2004204