Abstract
An effective strategy for the stereoselective synthesis of spiro isoxazolone-cyclohexenimines was developed using a bifunctional squaramide-catalysed vinylogous Michael addition/cyclization cascade reaction of 4-unsaturated isoxazol-5-ones and α,α-dicyanoalkenes. The atom-economical cascade process can proceed smoothly under extremely low catalyst loading (1 mol%) and mild conditions, and the corresponding products were obtained in moderate to good yields (45% to 90%) and enantioselectivitites (51% to 96% ee). Meanwhile, the scale-up reaction and transformation of the products were also demonstrated.
Original language | English |
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Pages (from-to) | 8572-8577 |
Number of pages | 6 |
Journal | Organic and Biomolecular Chemistry |
Volume | 19 |
Issue number | 39 |
DOIs | |
Publication status | Published - 21 Oct 2021 |
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Wang, Y., Niu, C., Xie, D. H., & Du, D. M. (2021). A bifunctional squaramide-catalysed enantioselective vinylogous Michael addition/cyclization cascade reaction of 4-unsaturated isoxazol-5-ones and α,α-dicyanoalkenes. Organic and Biomolecular Chemistry, 19(39), 8572-8577. https://doi.org/10.1039/d1ob01256h