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Paper | Special issue | Vol 84, No. 2, 2012, pp.879-892
Published online, 15th August, 2011
DOI: 10.3987/COM-11-S(P)66
Catalytic Asymmetric Amination of Oxindoles under Dinuclear Nickel Schiff Base Catalysis

Shinsuke Mouri, Zhihua Chen, Shigeki Matsunaga,* and Masakatsu Shibasaki*

*Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

Abstract

Catalytic asymmetric synthesis of 3-aminooxindoles with a tetrasubstituted carbon stereocenter is described. 1 mol% of homobimetallic (R)-Ni2-Schiff base complex 1 catalyzed asymmetric amination of 3-alkyl-substituted oxindoles with azodicarboxylates to give products in 89-99% yield and 87-99% ee. For 3-aryl-substituted oxindoles, 10 mol% of (R)-Ni2-Schiff base complex was required to obtain products in 66-98% ee. Postulated catalytic cycle as well as transformation of the products are also described.