title: Direct organocatalytic asymmetric aldol reaction of alpha-isothiocyanato imides to alpha-ketoesters under low ligand loading: a doubly stereocontrolled approach to cyclic thiocarbamates bearing chiral quaternary stereocenters.
abstract: The first doubly stereocontrolled organocatalytic asymmetric aldol reaction of alpha-isothiocyanato imides with alpha-ketoesters by using rosin-derived tertiary amine-thiourea under low ligand loading to form cyclic thiocarbamates bearing quaternary stereogenic centers with high levels of enantio- and diastereoselectivity (up to 99% ee, and 97:3 dr) is presented. This reaction provides a convenient doubly stereocontrolled method to access synthetic useful multiply substituted cyclic thiocarbamates with high optical purity.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Institute of Biochemistry and Molecular Biology, Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Lanzhou University, Lanzhou, 730000, China.
authors.forename: Xianxing
authors.initials: X
authors.lastname: Jiang
authors.forename: Gen
authors.initials: G
authors.lastname: Zhang
authors.forename: Dan
authors.initials: D
authors.lastname: Fu
authors.forename: Yiming
authors.initials: Y
authors.lastname: Cao
authors.forename: Fangfang
authors.initials: F
authors.lastname: Shen
authors.forename: Rui
authors.initials: R
authors.lastname: Wang
mesh_terms: D003500:Cyclization; D007094:Imides / Q000737:chemistry*; D017879:Isothiocyanates / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D013237:Stereoisomerism; D013859:Thiocarbamates / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007094:Imides; D017879:Isothiocyanates; D007659:Ketones; D008024:Ligands; D013859:Thiocarbamates