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Paper | Special issue | Vol 88, No. 1, 2014, pp.475-491
Published online, 23rd July, 2013
DOI: 10.3987/COM-13-S(S)60
Enantioselective Synthesis of Spirooxindoles via Direct Catalytic Asymmetric Aldol-Type Reaction of Isothiocyanato Oxindoles

Shota Kato, Motomu Kanai, and Shigeki Matsunaga*

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

Abstract

Direct catalytic asymmetric aldol-type reaction of aldehydes with isothiocyanato oxindoles is described. A dinuclear (S)-Ni2-Schiff base complex (0.1-10 mol %) efficiently catalyzed the addition of isothiocyanato oxindoles to aliphatic aldehydes, giving spirooxindole products in 80-99% ee and 81:19-91:9 dr. A Sr(O-iPr)2/Schiff base complex (10 mol %) was utilized for aryl aldehydes and spirooxindole products were obtained in 33-78% ee and 96:4-98:2 dr.