Abstract
A bifunctional squaramide-catalysed asymmetric Michael/cyclization cascade reaction of 3-hydroxyoxindoles with α,β-unsaturated N-acylated succinimides is disclosed. With quinine-derived squaramide as the catalyst, a broad range of the desired spirooxindole lactone derivatives bearing two contiguous stereocenters were obtained in good yields (up to 89%) with high diastereoselectivities (up to >95:5 dr) and excellent enantioselectivities (up to 99% ee).
Original language | English |
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Pages (from-to) | 6205-6213 |
Number of pages | 9 |
Journal | Organic and Biomolecular Chemistry |
Volume | 15 |
Issue number | 29 |
DOIs | |
Publication status | Published - 2017 |
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Ming, S., Zhao, B. L., & Du, D. M. (2017). Chiral squaramide-catalysed enantioselective Michael/cyclization cascade reaction of 3-hydroxyoxindoles with α,β-unsaturated: N -acylated succinimides. Organic and Biomolecular Chemistry, 15(29), 6205-6213. https://doi.org/10.1039/c7ob01307h