Enantioselective Michael/Hemiketalization Cascade Reactions between Hydroxymaleimides and 2-Hydroxynitrostyrenes for the Construction of Chiral Chroman-Fused Pyrrolidinediones
Abstract
:1. Introduction
2. Results and Discussion
2.1. Optimization of Reaction Conditions
2.2. Substrate Scope
2.3. Scaled-Up Synthesis
2.4. X-ray Diffraction Analysis
2.5. Controlled Reactions and Plausible Mechanism
3. Conclusions
4. Materials and Methods
4.1. General Information
4.2. Materials
4.3. Procedure for the Asymmetric Synthesis of Compounds 3
4.4. Procedure for the Scaled-Up Synthesis of Compound 3aa
4.5. Procedure for the Synthesis of Compound 4
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Entry | Solvent | Catalyst | Temperate (°C) | Yield b (%) | dr c | ee d (%) |
1 | CH2Cl2 | C1 | rt | 82 | >20:1 | 53 |
2 | CH2Cl2 | C1 | −16 | 80 | >20:1 | 87 |
3 | CH2Cl2 | C2 | rt | 85 | >20:1 | 55 |
4 | CH2Cl2 | C2 | −16 | 83 | >20:1 | 73 |
5 | CH2Cl2 | C3 | −16 | 88 | >20:1 | 96 |
6 | CH2Cl2 | C4 | −16 | 79 | >20:1 | 77 |
7 | CH2Cl2 | C5 | −16 | 77 | >20:1 | 95 |
8 | CH2Cl2 | C6 | −16 | 89 | >20:1 | 59 |
9 | CH2Cl2 | C7 | −16 | 82 | >20:1 | 81 |
10 | CH2Cl2 | C8 | −16 | 78 | >20:1 | 73 |
11 | CH2Cl2 | C9 | −16 | 90 | 16:1 | −69 |
12 | CH2Cl2 | C10 | −16 | 81 | 9:1 | 59 |
13 | DCE | C3 | −16 | 87 | >20:1 | 93 |
14 | Toluene | C3 | −16 | 80 | >20:1 | 85 |
15 | MeCN | C3 | −16 | 89 | >20:1 | 79 |
16 | CHCl3 | C3 | −16 | 83 | >20:1 | 87 |
17 | THF | C3 | −16 | trace | – | – |
18 e | CH2Cl2 | C3 | −16 | 86 | >20:1 | 95 |
19 f | CH2Cl2 | C3 | −16 | 80 | >20:1 | 89 |
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Xie, D.-H.; Niu, C.; Du, D.-M. Enantioselective Michael/Hemiketalization Cascade Reactions between Hydroxymaleimides and 2-Hydroxynitrostyrenes for the Construction of Chiral Chroman-Fused Pyrrolidinediones. Molecules 2022, 27, 5081. https://doi.org/10.3390/molecules27165081
Xie D-H, Niu C, Du D-M. Enantioselective Michael/Hemiketalization Cascade Reactions between Hydroxymaleimides and 2-Hydroxynitrostyrenes for the Construction of Chiral Chroman-Fused Pyrrolidinediones. Molecules. 2022; 27(16):5081. https://doi.org/10.3390/molecules27165081
Chicago/Turabian StyleXie, Dong-Hua, Cheng Niu, and Da-Ming Du. 2022. "Enantioselective Michael/Hemiketalization Cascade Reactions between Hydroxymaleimides and 2-Hydroxynitrostyrenes for the Construction of Chiral Chroman-Fused Pyrrolidinediones" Molecules 27, no. 16: 5081. https://doi.org/10.3390/molecules27165081