Practical and Efficient Organocatalytic Enantioselective [alpha]-Hydroxyamination Reactions of [beta]-Ketoamides

The first organocatalytic general, efficient and highly enantioselective [alpha]-hydroxyamination reactions of [beta]-ketoamides with nitrosobenzene are described using a thiourea/tertiary amine bifunctional catalyst. Significantly, the products were obtained in high enantiomeric purity using a low...

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Bibliographic Details
Published inChemCatChem Vol. 5; no. 5; p. 1192
Main Authors Mailhol, Damien, Castillo, Juan-Carlos, Mohanan, Kishor, Abonia, Rodrigo, Coquerel, Yoann, Rodriguez, Jean
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 01.05.2013
Subjects
Beta
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Summary:The first organocatalytic general, efficient and highly enantioselective [alpha]-hydroxyamination reactions of [beta]-ketoamides with nitrosobenzene are described using a thiourea/tertiary amine bifunctional catalyst. Significantly, the products were obtained in high enantiomeric purity using a low catalyst loading, and in the context of sustainable development, the full reaction mixture, including solvent, catalyst and excess substrate, can be recycled without significant erosion in the efficiency and enantioselectivity of the reaction. The described catalytic transformations secure a practical synthetic access to stereodefined and conformationally constrained [alpha]-amino acid derivatives exhibiting a quaternary chiral center at the [alpha] position. [PUBLICATION ABSTRACT]
ISSN:1867-3880
1867-3899
DOI:10.1002/cctc.201200723