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Communication | Special issue | Vol 95, No. 2, 2017, pp.761-767
Published online, 20th February, 2017
DOI: 10.3987/COM-16-S(S)86
Facile Synthesis of Spirooxindoles via an Enantioselective Organocatalyzed Sequential Reaction of Oxindoles with Ynone

Shinobu Takizawa,* Kenta Kishi, Miki Kusaba, Bai Jianfei, Takeyuki Suzuki, and Hiroaki Sasai*

*The Institute of Scientific and Industrial Research (ISIR), Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan


The reaction of oxindole 1a with phenylprop-2-yn-1-one (2a) was promoted by the chiral multifunctional phosphine catalyst 4a derived from (S)-valine, giving spirooxindole 3a in good yield and high enantioselectivity. The obtained spirooxindole forms a common scaffold of a vast number of natural products exhibiting various biological activities.