Practical and Efficient Organocatalytic Enantioselective α- Hydroxyamination Reactions of β-Ketoamides - Aix-Marseille Université Access content directly
Journal Articles ChemCatChem Year : 2013

Practical and Efficient Organocatalytic Enantioselective α- Hydroxyamination Reactions of β-Ketoamides

Damien Mailhol
  • Function : Author
Juan-Carlos Castillo
  • Function : Author
Kishor Mohanan
  • Function : Author
Yoann Coquerel
Jean Rodriguez
  • Function : Author
  • PersonId : 921781

Abstract

The first organocatalytic general, efficient and highly enantioselective α-hydroxyamination reactions of β-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 α−amino acid derivatives exhibiting a quaternary chiral center at the α position.

Dates and versions

hal-00861707 , version 1 (13-09-2013)

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Damien Mailhol, Juan-Carlos Castillo, Kishor Mohanan, Rodrigo Abonia, Yoann Coquerel, et al.. Practical and Efficient Organocatalytic Enantioselective α- Hydroxyamination Reactions of β-Ketoamides. ChemCatChem, 2013, 5, pp.1192-1199. ⟨10.1002/cctc.201200723⟩. ⟨hal-00861707⟩
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