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Synfacts 2010(8): 0910-0910  
DOI: 10.1055/s-0030-1257771
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Scandium-Catalyzed Asymmetric α-Amination of 3-Substituted 2-Oxindoles

Contributor(s): Mark Lautens, Chit Tsui
Z. Yang, Z. Wang, S. Bai, K. Shen, D. Chen, X. Liu, L. Lin, X. Feng*
Sichuan University, Chengdu, P. R. of China
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Publikationsverlauf

Publikationsdatum:
22. Juli 2010 (online)

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Significance

The authors have developed a highly enantioselective α-amination of 3-substituted oxindoles 1 with diazodicarboxylates 2 using a chiral Sc(OTf)3/N,N′-dioxide complex as catalyst. The corresponding 3-amino-2-oxindoles 3 can be obtained in excellent yields (up to 98%) and enantioselectivities (up to 98% ee). A wide range of substrates are tolerated, even with only 0.5 mol% catalyst loading.