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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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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cited_by cdi_FETCH-LOGICAL-a381t-54022917d17519b25a48f00f4cad28d0fb1cf30b7fdcd5eebdf56d803923450d3
cites cdi_FETCH-LOGICAL-a381t-54022917d17519b25a48f00f4cad28d0fb1cf30b7fdcd5eebdf56d803923450d3
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container_issue 18
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container_title Journal of organic chemistry
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creator López-Cantarero, Jesús
Cid, M. Belén
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Jørgensen, Karl Anker
description 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.
doi_str_mv 10.1021/jo071186o
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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
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
title Intriguing Behavior of Cinchona Alkaloids in the Enantioselective Organocatalytic Hydroxyamination of α-Substituted-α-cyanoacetates
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