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  • Title: Highly efficient and stereocontrolled construction of 3,3'-pyrrolidonyl spirooxindoles via organocatalytic domino Michael/cyclization reaction.
    Author: Liu XL, Han WY, Zhang XM, Yuan WC.
    Journal: Org Lett; 2013 Mar 15; 15(6):1246-9. PubMed ID: 23452297.
    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).
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