Enantioselective Arylation of 2-Methylacetoacetates Catalyzed by CuI/trans-4-Hydroxy-l-proline at Low Reaction Temperatures
- 23 November 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (50) , 16050-16051
- https://doi.org/10.1021/ja066991j
Abstract
CuI/trans-4-hydroxy-l-proline-catalyzed coupling reaction of 2-iodotrifluoroacetanilides with 2-methylacetoacetates took place at −45 °C to create α-aryl all-carbon quaternary centers enantioselectively. Up to 93% ee was achieved when tert-butyl ester was used. The combination of ligand, ortho substituent (participation of NHCOCF3), and solvent effects was shown to account for these unprecedentedly mild reaction conditions.Keywords
This publication has 14 references indexed in Scilit:
- Highly Selective Room-Temperature Copper-Catalyzed C−N Coupling ReactionsJournal of the American Chemical Society, 2006
- Four Novel Gelsenicine-Related Oxindole Alkaloids from the Leaves of Gelsemium elegans Benth.Organic Letters, 2006
- Molybdenum-Catalyzed Asymmetric Allylation of 3-Alkyloxindoles: Application to the Formal Total Synthesis of (−)-PhysostigmineJournal of the American Chemical Society, 2006
- Mild Ullmann‐Type Biaryl Ether Formation Reaction by Combination of ortho‐Substituent and Ligand EffectsAngewandte Chemie International Edition in English, 2006
- CuI/l-Proline-Catalyzed Coupling Reactions of Aryl Halides with Activated Methylene CompoundsOrganic Letters, 2005
- Asymmetric Synthesis of Pyrrolidinoindolines. Application for the Practical Total Synthesis of (−)-PhenserineJournal of the American Chemical Society, 2004
- Preparation of cruciferous phytoalexin related metabolites, (−)-dioxibrassinin and (−)-3-cyanomethyl-3-hydroxyoxindole, and determination of their absolute configurations by vibrational circular dichroism (VCD)Tetrahedron Letters, 2003
- Catalytic Enantioselective Synthesis of Quaternary Stereocenters via Intermolecular C-Acylation of Silyl Ketene Acetals: Dual Activation of the Electrophile and the NucleophileJournal of the American Chemical Society, 2003
- Towards Perfect Asymmetric Catalysis: Additives and CocatalystsAngewandte Chemie International Edition in English, 1999
- Asymmetric Arylation of Ketone EnolatesJournal of the American Chemical Society, 1998