Asymmetric Synthesis of 1,3-Oxazolidine Derivatives with Multi-Component Reaction and Research of Kinetic Resolution
Abstract
:1. Introduction
2. Results and Discussion
Entry | Solvent | Catal. | T (°C) | Yield (%) b | d.r. c | ee (%) d |
---|---|---|---|---|---|---|
1 | CH2Cl2 | 4a | 18 | 5 | 2:1 | 10 |
2 | CH2Cl2 | 4b | 18 | 13 | 3:1 | 15 |
3 | CH2Cl2 | 4b | −10 | 13 | 2:1 | 30 |
4 e | CH2Cl2 | 4c/Ti(IV) | −40 | 13 | 3:1 | 41 |
5 e | PhCH3 | 4c/Ti(IV) | −40 | 15 | 4:1 | 60 |
6 e | PhCH3 | 4c/Ti(IV) | −40 | 50 | 4:1 | 61 |
7 f | PhCH3 | 4c/Ti(IV) | −40 | 53 | 11:1 | 72 |
8 f | PhCH3 | 4d/Ti(IV) | −40 | 36 | 11:1 | 72 |
9 f | PhCH3 | 4c/Ti(IV) | −55 | 30 | 12:1 | 73 |
10 f | PhCH3 | 4c/Ti(IV) | −70 | 15 | 12:1 | 73 |
Entry | 3 | R1 | R2 | Yield (%) b | d.r. c | ee (%) d |
---|---|---|---|---|---|---|
1 | 3a | CH3O | CH2Cl | 52 | 12:1 | 43 |
2 | 3b | Cl | CH2Cl | 50 | 10:1 | 69 |
3 | 3c | CH3CH2O | CH2Cl | 47 | 10:1 | 39 |
4 | 3d | CH3O | CH2OCH(CH3)2 | 56 | 4:1 | 43 |
5 | 3e | CH3O | CH2O(CH2)3CH3 | 46 | 1.5:1 | 71 |
6 | 3f | CH3CH2O | CH2O(CH2)3CH3 | 53 | 3:1 | 34 |
7 | 3g | CH3CH2O | CH2OCH(CH3)2 | 53 | 3:1 | 72 |
8 | 3h | Cl | CH2O(CH2)3CH3 | 48 | 3:1 | 69 |
9 | 3i | Cl | CH2OCH(CH3)2 | 54 | 4:1 | 90 |
10 | 3j | CH3O | Ph | 42 | 1.7:1 | 84.6 |
11 | 3k | NO2 | CH2Cl | trace | ― | ― |
3. Experimental Section
3.1. General Procedure for the Synthesis of All 1,3-Oxazolidines
3.2. Characterization Data for All of the Compounds
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Hong, X.-W.; Zhou, Y.-Q.; Bai, C.-B.; Wang, N.-X.; Xing, Y.; Zhang, W.; Wang, Y.-J.; Lan, X.-W.; Xie, Y.; Li, Y.-H. Asymmetric Synthesis of 1,3-Oxazolidine Derivatives with Multi-Component Reaction and Research of Kinetic Resolution. Molecules 2015, 20, 17208-17220. https://doi.org/10.3390/molecules200917208
Hong X-W, Zhou Y-Q, Bai C-B, Wang N-X, Xing Y, Zhang W, Wang Y-J, Lan X-W, Xie Y, Li Y-H. Asymmetric Synthesis of 1,3-Oxazolidine Derivatives with Multi-Component Reaction and Research of Kinetic Resolution. Molecules. 2015; 20(9):17208-17220. https://doi.org/10.3390/molecules200917208
Chicago/Turabian StyleHong, Xiao-Wei, Yu-Qiang Zhou, Cui-Bing Bai, Nai-Xing Wang, Yalan Xing, Wei Zhang, Yan-Jing Wang, Xing-Wang Lan, Yu Xie, and Yi-He Li. 2015. "Asymmetric Synthesis of 1,3-Oxazolidine Derivatives with Multi-Component Reaction and Research of Kinetic Resolution" Molecules 20, no. 9: 17208-17220. https://doi.org/10.3390/molecules200917208