Organic Letters 2012-06-01

Catalytic asymmetric sulfenylation of unprotected 3-substituted oxindoles.

Yunfei Cai, Jun Li, Weiliang Chen, Mingsheng Xie, Xiaohua Liu, Lili Lin, Xiaoming Feng

Index: Org. Lett. 14(11) , 2726-9, (2012)

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Abstract

Catalytic asymmetric sulfenylation of unprotected 3-substituted oxindoles has been developed via cooperative catalysis of a chiral N,N'-dioxide-Sc(OTf)(3) complex and a Brønsted base. Utilizing readily available N-(phenylthio)phthalimide as the sulfur source, a wide range of optically active 3-phenylthiooxindoles were obtained in excellent yields with excellent enantioselectivities under mild reaction conditions.