Citation: Sun jianan, Li Yanan, Gui Yang, Xu Youguo, Zha Zhenggen, Wang Zhiyong. Copper(Ⅱ)-catalyzed enantioselective conjugate addition of nitro esters to 2-enoyl-pyridine N-oxides[J]. Chinese Chemical Letters, ;2019, 30(3): 569-572. doi: 10.1016/j.cclet.2018.11.024 shu

Copper(Ⅱ)-catalyzed enantioselective conjugate addition of nitro esters to 2-enoyl-pyridine N-oxides

Hefei National Laboratory for Physical Sciences at Microscale, CAS Key Laboratory of Soft Matter Chemistry & Center for Excellence in Molecular Synthesis of Chinese Academy of Sciences, Collaborative Innovation Center of Suzhou Nano Science and Technology & School of Chemistry and Materials Science, University of Science and Technology of China, Hefei 230026, China

zwang3@ustc.edu.cn

Received Date: 19 September 2018
Revised Date: 11 November 2018
Accepted Date: 19 November 2018
Available Online: 29 March 2018

Figures(4)

A highly enantioselective Michael addition of nitro esters to 2-enoyl-pyridine N-oxides was developed by using chiral copper catalysts. The Michael addition products can be obtained in high yields and with up to 96% ee. Moreover, asymmetric Michael addition product of nitromethane to 2-enoyl-pyridine N-oxides can be obtained in one step. An analogue of nicotine, dihydro-2H-pyrrol 4b was synthesized with this developed method.
- Michael reaction,
- Asymmetric catalysis,
- Copper catalysis,
- Nitro esters,
- 2-Enoyl-pyridine N-oxides
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