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Enantioselective [3+2] annulation of isatin-derived MBH-carbonates and 3-nitroindoles enabled by a bifunctional DMAP-thiourea. 2020

Ming-Shun Mei, and Yu-Hui Wang, and Qing Hu, and Qing-Hua Li, and Da-Yu Shi, and Dingding Gao, and Guangbo Ge, and Guo-Qiang Lin, and Ping Tian
The Research Center of Chiral Drugs, Innovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine, 1200 Cailun Road, Shanghai 201203, China. gaodingding@shutcm.edu.cn tianping@shutcm.edu.cn tianping@sioc.ac.cn.

A highly enantioselective [3+2] annulation of isatin-derived Morita-Baylis-Hillman (MBH) carbonates and 3-nitroindoles was enabled by a chiral DMAP-thiourea bifunctional catalyst, affording the corresponding polycyclic spirooxindoles bearing three consecutive stereocenters with good to excellent yields and enantioselectivities. Transformations of the annulation product were subsequently elaborated and the preliminary biological assays demonstrated that these artificial spirooxindoles potentially inhibited pancreatic lipase in a dose-dependent manner.

UI MeSH Term Description Entries
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D006574 Heterocyclic Compounds, 2-Ring A class of heterocyclic compounds that include a two-ring fused structure. Both aromatic and non-aromatic ring structures are included in this category. Fused Heterocyclic Compounds, Two-Ring,Two Ring Heterocyclic Compounds,2-Ring Heterocyclic Compounds,Fused Heterocyclic Compounds, Two Ring,Heterocyclic Compounds, 2 Ring
D000078183 Oxindoles Benzopyrroles with the nitrogen at the number one carbon adjacent to the benzyl and a carbonyl at the pyrrole ring typically at the 2-position. Ajmalicine Oxindole,Ajmalicine Oxindoles,Ajmalicine-Type Oxindole,Ajmalicine-Type Oxindoles,Indolinone,Indolinone Derivative,Macroline Oxindole,Macroline Oxindoles,Macroline-Type Oxindole,Macroline-Type Oxindoles,Oxazolidinone Derivative,Oxindole Alkaloid,Oxindole Alkaloid Derivative,Oxindole Derivative,Indolinone Derivatives,Indolinones,Oxazolidinone Derivatives,Oxindole Alkaloid Derivatives,Oxindole Alkaloids,Oxindole Derivatives,Ajmalicine Type Oxindole,Ajmalicine Type Oxindoles,Alkaloid Derivative, Oxindole,Alkaloid, Oxindole,Derivative, Indolinone,Derivative, Oxazolidinone,Derivative, Oxindole,Derivative, Oxindole Alkaloid,Macroline Type Oxindole,Macroline Type Oxindoles,Oxindole, Ajmalicine,Oxindole, Ajmalicine-Type,Oxindole, Macroline,Oxindole, Macroline-Type,Oxindoles, Ajmalicine,Oxindoles, Ajmalicine-Type,Oxindoles, Macroline,Oxindoles, Macroline-Type
D013141 Spiro Compounds Cyclic compounds that include two rings which share a single atom (usually a carbon). The simplest example of this type of compound is Spiro[2.2]pentane, which looks like a bow tie. Compounds, Spiro
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D013890 Thiourea A photographic fixative used also in the manufacture of resins. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance may reasonably be anticipated to be a carcinogen (Merck Index, 9th ed). Many of its derivatives are ANTITHYROID AGENTS and/or FREE RADICAL SCAVENGERS.

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