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- Title
Enantioselective Michael/Hemiketalization Cascade Reactions between Hydroxymaleimides and 2-Hydroxynitrostyrenes for the Construction of Chiral Chroman-Fused Pyrrolidinediones.
- Authors
Xie, Dong-Hua; Niu, Cheng; Du, Da-Ming
- 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.
- Subjects
ORGANOCATALYSIS; CATALYSIS; NITROALKENES
- Publication
Molecules, 2022, Vol 27, Issue 16, p5081
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules27165081