Abstract
In this paper, the organocatalytic asymmetric Michael addition/hemiketalization cascade reactions between hydroxymaleimides and 2-hydroxynitrostyrenes were developed, which provided a new protocol for building a chiral ring-fused chroman skeleton. This squaramide-catalyzed cascade reaction provided chiral chroman-fused pyrrolidinediones with three contiguous stereocenters in good to high yields (up to 88%), with excellent diastereoselectivities (up to >20:1 dr) and enantioselectivities (up to 96% ee) at −16 °C. Moreover, a scale-up synthesis was also carried out, and a possible reaction mechanism was proposed.
Original language | English |
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Article number | 5081 |
Journal | Molecules |
Volume | 27 |
Issue number | 16 |
DOIs | |
Publication status | Published - Aug 2022 |
Keywords
- asymmetric catalysis
- cascade reaction
- chroman
- hydroxymaleimide
- organocatalysis
- pyrrolidinedione
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Xie, D. H., Niu, C., & Du, D. M. (2022). Enantioselective Michael/Hemiketalization Cascade Reactions between Hydroxymaleimides and 2-Hydroxynitrostyrenes for the Construction of Chiral Chroman-Fused Pyrrolidinediones. Molecules, 27(16), Article 5081. https://doi.org/10.3390/molecules27165081