title: Catalytic Asymmetric Construction of Vicinal Tetrasubstituted Stereocenters by the Mannich Reaction of Linear α-Substituted Monothiomalonates with Isatin N-Boc Ketimines.
abstract: A highly diastereo- and enantioselective method for the construction of vicinal tetrasubstituted stereocenters through the first catalytic asymmetric Mannich reaction of linear α-substituted MTMs with isatin N-Boc ketimines has been developed. This protocol provides atom-economic synthesis of less accessible 3-aminooxindoles bearing vicinal tetrasubstituted stereocenters. Notably, it also constitutes the first example of stereoselective synthesis of β-amino thioesters bearing vicinal tetrasubstituted stereocenters.
authors.affiliation: †Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China.
authors.forename: Teng
authors.initials: T
authors.lastname: Liu
authors.affiliation: †Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China.
authors.forename: Weiwei
authors.initials: W
authors.lastname: Liu
authors.affiliation: ‡Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China.
authors.forename: Xiaonian
authors.initials: X
authors.lastname: Li
authors.affiliation: †Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China.
authors.forename: Fangzhi
authors.initials: F
authors.lastname: Peng
authors.affiliation: †Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China.
authors.forename: Zhihui
authors.initials: Z
authors.lastname: Shao
mesh_terms: D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D007510:Isatin / Q000737:chemistry*; D008314:Malonates / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007097:Imines; D008314:Malonates; D009570:Nitriles; C542835:ketimine; D007510:Isatin