title: A cinchona alkaloid catalyzed enantioselective sulfa-Michael/aldol cascade reaction of isoindigos: construction of chiral bispirooxindole tetrahydrothiophenes with vicinal quaternary spirocenters.
abstract: A cinchona alkaloid catalyzed diastereoselective and enantioselective sulfa-Michael/aldol cascade reaction between 1,4-dithiane-2,5-diol and isoindigos has been successfully developed to afford the highly congested bispirooxindole tetrahydrothiophenes with vicinal quaternary spirocenters in high yields (up to 91%), excellent diastereoselectivities (up to >20 : 1 dr), and good enantioselectivities (up to 98% ee). Some synthetic transformations of the reaction products were also studied.
authors.affiliation: Key Laboratory of Asymmetric Synthesis & Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, P.R. China. wlxioc@cioc.ac.cn penglin@cioc.ac.cn.
authors.forename: Yong-Yuan
authors.initials: YY
authors.lastname: Gui
authors.forename: Jian
authors.initials: J
authors.lastname: Yang
authors.forename: Liang-Wen
authors.initials: LW
authors.lastname: Qi
authors.forename: Xiao
authors.initials: X
authors.lastname: Wang
authors.forename: Fang
authors.initials: F
authors.lastname: Tian
authors.forename: Xiao-Nian
authors.initials: XN
authors.lastname: Li
authors.forename: Lin
authors.initials: L
authors.lastname: Peng
authors.forename: Li-Xin
authors.initials: LX
authors.lastname: Wang
mesh_terms: D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry*; D018360:Crystallography, X-Ray; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D002930:Cinchona Alkaloids; D007211:Indoles; D013141:Spiro Compounds; D013876:Thiophenes; C049010:isoindigotin