title: The enantioselective construction of chiral spirooxindole-based 4-thiazolidinone via asymmetric catalytic formal [3+2] annulation using a bifunctional catalyst.
abstract: 4-Thiazolidinone is regarded as a privileged structural unit in bioactive compounds. However, there is still no example of a catalytic method for the synthesis of chiral 4-thiazolidinone until now. We reported herein a facile and efficient method for the construction of chiral spirooxindole-based 4-thiazolidinone. This methodology is based on the asymmetric formal [3+2] annulation of 1,4-dithiane-2,5-diol to ketimines which is followed by simple oxidation, featuring a broad substrate scope with high enantioselectivity (up to 98% ee). The method has been successfully applied to the synthesis of a novel class of mycobacterium tuberculosis inhibitor-spirooxindole based 4-thiazolidinone.
authors.affiliation: Department of Chemistry, Dalian University of Technology, 2 Linggong Road, Dalian, 116024, P. R. China. duxin@.dlut.edu.cn.
authors.forename: Ping
authors.initials: P
authors.lastname: Cheng
authors.forename: Wengang
authors.initials: W
authors.lastname: Guo
authors.forename: Ping
authors.initials: P
authors.lastname: Chen
authors.forename: Yan
authors.initials: Y
authors.lastname: Liu
authors.forename: Xin
authors.initials: X
authors.lastname: Du
authors.forename: Can
authors.initials: C
authors.lastname: Li
mesh_terms: D002384:Catalysis; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013844:Thiazoles / Q000737:chemistry*
chemical_list: D013141:Spiro Compounds; D013844:Thiazoles