Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 22, Pages 6632-6637Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201000126
Keywords
amination; asymmetric catalysis; dioxides; oxindoles; scandium
Categories
Funding
- National Natural Science Foundation of China [20732003, 20872097]
- PCSIRT [IRT0846]
- National Basic Research Program of China (973 Program) [2010CB833300]
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A highly enantioselective alpha-amination of 3-substituted oxindoles with azodicarboxylates catalyzed by a chiral Sc(OTf)(3)/N,N'-dioxide complex (Tf: triflate) has been developed and affords the corresponding 3-amino-2-oxindole derivatives in high yields (up to 98%) with excellent enantioselectivities (up to 99% ee). The procedure is capable of tolerating a relatively wide range of substrates, and excellent results (92-96% ee) can also be obtained, even in the presence of 0.5 mol% of catalyst loading under mild conditions. These results showed the potential value of the catalytic approach. Moreover, with high synthetic versatility, the product could be easily transformed into optically active 3-amino-3-methyloxindole bearing a chiral quaternary stereogenic center.
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