Intriguing Behavior of Cinchona Alkaloids in the Enantioselective Organocatalytic Hydroxyamination of α-Substituted-α-cyanoacetates

The cinchona alkaloid quinine promotes the enantioselective nitroso-aldol reaction between α-aryl-α-cyanoacetates and nitrosobenzene to give the hydroxyamination products with total chemoselectivity. Treatment of the reaction mixture with Zn/AcOH affords the corresponding amines in high yield and mo...

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Bibliographic Details
Published in:Journal of organic chemistry 2007-08, Vol.72 (18), p.7062-7065
Main Authors: López-Cantarero, Jesús, Cid, M. Belén, Poulsen, Thomas B, Bella, Marco, Ruano, José Luis García, Jørgensen, Karl Anker
Format: Article
Language:English
Subjects:
Catalysis
Catalysts: preparations and properties
Chemistry
Exact sciences and technology
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary:The cinchona alkaloid quinine promotes the enantioselective nitroso-aldol reaction between α-aryl-α-cyanoacetates and nitrosobenzene to give the hydroxyamination products with total chemoselectivity. Treatment of the reaction mixture with Zn/AcOH affords the corresponding amines in high yield and moderate enantioselectivity. An unusual effect on the enantioselectivity was observed with the catalyst loading and solvent. A reductive protocol allows the construction of an optically active 1,2-diamine moiety bearing a quaternary center.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo071186o