title: Highly efficient and stereocontrolled construction of 3,3'-pyrrolidonyl spirooxindoles via organocatalytic domino Michael/cyclization reaction.
abstract: A wide range of structurally diverse 3,3'-thiopyrrolidonyl spirooxindoles bearing three contiguous stereogenic centers can be smoothly obtained via a domino Michael/cyclization reaction between 3-isothiocyanato oxindoles and 3-methyl-4-nitro-5-alkenyl-isoxazoles with commercially available quinine as the catalyst under mild conditions. The protocol is significantly characterized by high reactivity, a low catalyst loading (1 mol %), and an excellent diastereo- and enantioselectivity (up to >99:1 dr and 98% ee).
authors: National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
authors: Xiong-Li
authors: XL
authors: Liu
authors: Wen-Yong
authors: WY
authors: Han
authors: Xiao-Mei
authors: XM
authors: Zhang
authors: Wei-Cheng
authors: WC
authors: Yuan
mesh_terms: D002384:Catalysis; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D007555:Isoxazoles / Q000737:chemistry*; D015394:Molecular Structure; D000078183:Oxindoles; D011803:Quinine / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006576:Heterocyclic Compounds, 4 or More Rings; D007211:Indoles; D007555:Isoxazoles; D000078183:Oxindoles; D013141:Spiro Compounds; C022960:2-oxindole; D011803:Quinine