Highly enantioselective organocatalytic α-amination reactions of aryl oxindoles: developing designer multifunctional alkaloid catalysts.
An enantioselective α-amination of aryl oxindoles catalyzed by a dimeric quinidine has been developed. The reaction is general, broad in substrate scope, and affords the desired products in good yields with good to excellent enantioselectivities. This study provides the first examples of a general organocatalytic method for the creation of nitrogen-containing, tetrasubstituted chiral centers at C(3) of various aryl oxindoles. Furthermore, new catalysts and insights into structural elements of the catalysts that significantly influence enantioselectivities are disclosed.
The Skaggs Institute for Chemical Biology and the Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Tommy
T
Bui
Gloria
G
Hernández-Torres
Ciro
C
Milite
Carlos F
CF
Barbas
D000470:Alkaloids / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D019281:Dimerization; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D000078183:Oxindoles; D013237:Stereoisomerism
D000470:Alkaloids; D007211:Indoles; D000078183:Oxindoles; C022960:2-oxindole