Abstract
A class of o-sulfonylaminostyryl isoxazole synthons were designed and demonstrated to be useful building blocks in asymmetric cascade aza-Michael/Michael reaction with 3-olefinic oxindoles. This squaramide-catalysed cascade reaction afforded structurally complex isoxazole-containing spirooxindole tetrahydroquinolines bearing three contiguous stereocenters in good to excellent yields (up to 99%) with high diastereoselectivities (up to >20 : 1 dr) and enantioselectivities (up to 88% ee). Moreover, the gram-scale synthesis and synthetic transformations were also demonstrated.
Original language | English |
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Pages (from-to) | 5582-5588 |
Number of pages | 7 |
Journal | Organic and Biomolecular Chemistry |
Volume | 20 |
Issue number | 28 |
DOIs | |
Publication status | Published - 5 Jul 2022 |
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Li, T. H., Niu, C., & Du, D. M. (2022). Enantioselective synthesis of isoxazole-containing spirooxindole tetrahydroquinolines via squaramide-catalysed cascade reactions. Organic and Biomolecular Chemistry, 20(28), 5582-5588. https://doi.org/10.1039/d2ob00864e