Abstract
A highly efficient method for the construction of oxindole-pyrrolidone-thiazolidinone bispirocyclic heterocycles bearing three contiguous chiral centers including two quaternary one via a Michael/cyclization cascade reaction has been developed. Using bifunctional cinchona-derived squaramide as catalyst, the reactions of 3-isothiocyanato oxindoles with unsaturated thiazolidinone derivatives proceeded smoothly under mild reaction conditions to afford a series of complex chiral oxindole-pyrrolidone-thiazolidinone bispirocyclic heterocycles in high yields (up to 99%) with excellent diastereo- and enantioselectivities (up to >99:1 dr, >99% ee).
Original language | English |
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Pages (from-to) | 1535-1545 |
Number of pages | 11 |
Journal | Synthesis |
Volume | 50 |
Issue number | 7 |
DOIs | |
Publication status | Published - 3 Apr 2018 |
Keywords
- 3-isothiocyanato oxindoles
- Michael/cyclization cascade reaction
- asymmetric catalysis
- organocatalysis
- thiazolidinone derivatives
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Song, Y. X., & Du, D. M. (2018). Squaramide-Catalyzed Asymmetric Michael/Cyclization Cascade Reaction of Unsaturated Thiazolidinones and 3-Isothiocyanato Oxindoles: Synthesis of New Bispirocyclic Heterocycles. Synthesis, 50(7), 1535-1545. https://doi.org/10.1055/s-0036-1591527