title: Facile creation of 3-substituted-3-hydroxy-2-oxindoles by arginine-catalyzed aldol reactions of α,β-unsaturated ketones with isatins.
abstract: An efficient approach for the synthesis of 3-substituted-3-hydroxy-2-oxindoles has been achieved via an aldol reaction of α,β-unsaturated ketones and isatins using arginine as an organocatalyst. A range of 3-substituted-3-hydroxy-2-oxindoles were obtained in moderate to high (up to 99%) yields. These 3-substituted-3-hydroxy-2-oxindoles with an additional enone moiety provide an opportunity for further elaboration of the products and for potentially interesting biological activities. In addition, the formation of 3-substituted-3-hydroxy-2-oxindole 3a was conﬁrmed by X-ray crystallography. The possible reaction mechanism reveals that the reaction proceeds via a double action process.
authors.affiliation: State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, China. liujie2011@scu.edu.cn.
authors.forename: Tingting
authors.initials: T
authors.lastname: Yan
authors.forename: Xiaoyan
authors.initials: X
authors.lastname: Wang
authors.forename: Hongbao
authors.initials: H
authors.lastname: Sun
authors.forename: Jie
authors.initials: J
authors.lastname: Liu
authors.forename: Yongmei
authors.initials: Y
authors.lastname: Xie
mesh_terms: D001120:Arginine / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D007510:Isatin / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D000078183:Oxindoles
chemical_list: D007211:Indoles; D007659:Ketones; D000078183:Oxindoles; C022960:2-oxindole; D007510:Isatin; D001120:Arginine