Endo-Selective Construction of Spiro-[butyrolactone-pyrrolidine] via Ag(I)/CAAA-Amidphos-Catalyzed 1,3-Dipolar Cycloaddition between Azomethine Ylides and α-Methylene-γ-Butyrolactone
Abstract
:1. Introduction
2. Results and Discussion
2.1. Optimization of the 1,3-Dipole Cycloaddition Reaction Conditions
2.2. Study on Substrate Adaptability
2.3. Study on the Construction of Spiro Pyrrolidines by the Three-Component One-Pot Method
3. Materials and Methods
3.1. Materials
3.2. General Synthesis Methods of 4a–4p
3.3. General Synthesis Methods of 6a–6g via Three-Component “One-Pot”
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Entry | Precat. | MLn | Temp. [°C] | Time [h] | Yield [%] b | Ee [%] c |
---|---|---|---|---|---|---|
1 | 1a | Ag2O | rt | 2.5 | 74 | 14 |
2 | 1b | Ag2O | rt | 2 | 92 | 84 |
3 | 1c | Ag2O | rt | 2 | 91 | 76 |
4 | 1d | Ag2O | rt | 2 | 93 | 87 |
5 | 1d | Ag2CO3 | rt | 2 | 78 | 84 |
6 | 1d | AgF | rt | 2 | 80 | 45 |
7 | 1d | AgOAc | rt | 18 | 61 | 4 |
8 | 1d | AgOTf | rt | 24 | trace | - |
9 | 1d | Cu(OTf)2 | rt | 24 | trace | - |
10 | 1d | Ag2O | −20 | 6 | 90 | 92 |
11 d | 1d | Ag2O | −20 | 0.7 | 94 | 93 |
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Hou, Q.; You, Y.; Song, X.; Wang, Y.; Chen, K.; Wang, H. Endo-Selective Construction of Spiro-[butyrolactone-pyrrolidine] via Ag(I)/CAAA-Amidphos-Catalyzed 1,3-Dipolar Cycloaddition between Azomethine Ylides and α-Methylene-γ-Butyrolactone. Catalysts 2020, 10, 28. https://doi.org/10.3390/catal10010028
Hou Q, You Y, Song X, Wang Y, Chen K, Wang H. Endo-Selective Construction of Spiro-[butyrolactone-pyrrolidine] via Ag(I)/CAAA-Amidphos-Catalyzed 1,3-Dipolar Cycloaddition between Azomethine Ylides and α-Methylene-γ-Butyrolactone. Catalysts. 2020; 10(1):28. https://doi.org/10.3390/catal10010028
Chicago/Turabian StyleHou, Qinglin, Yaoyao You, Xinluo Song, Yingxia Wang, Ke Chen, and Haifei Wang. 2020. "Endo-Selective Construction of Spiro-[butyrolactone-pyrrolidine] via Ag(I)/CAAA-Amidphos-Catalyzed 1,3-Dipolar Cycloaddition between Azomethine Ylides and α-Methylene-γ-Butyrolactone" Catalysts 10, no. 1: 28. https://doi.org/10.3390/catal10010028
APA StyleHou, Q., You, Y., Song, X., Wang, Y., Chen, K., & Wang, H. (2020). Endo-Selective Construction of Spiro-[butyrolactone-pyrrolidine] via Ag(I)/CAAA-Amidphos-Catalyzed 1,3-Dipolar Cycloaddition between Azomethine Ylides and α-Methylene-γ-Butyrolactone. Catalysts, 10(1), 28. https://doi.org/10.3390/catal10010028