Citation: Xian-Dong Zhai, Zhong-Duo Yang, Zhi Luo, Hong-Tao Xu. Asymmetric catalyzed intramolecular aza-Michael reaction mediated by quinine-derived primary amines[J]. Chinese Chemical Letters, ;2017, 28(8): 1793-1797. doi: 10.1016/j.cclet.2017.04.017 shu

Asymmetric catalyzed intramolecular aza-Michael reaction mediated by quinine-derived primary amines

a.
School of Life Science and Engineering, Lanzhou University of Technology, Lanzhou 730050, China
b.
Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China

Corresponding author: Zhong-Duo Yang, yangzhongduo@126.com
Received Date: 13 January 2017
Revised Date: 7 April 2017
Accepted Date: 17 April 2017
Available Online: 22 August 2017

Figures(1)

An intramolecular organocatalytic enantioselective aza-Michael reaction of carbamates, sulfonamides and acetamides to α, β-unsaturated ketones was developed. This process is promoted by 9-amino-9-deoxy-epi-quinine and diphenyl hydrogen phosphate to afford a straightforward and expeditious synthesis of several synthetically useful five-and six-membered heterocycles with excellent enantioselectivity (92%-97.5% ee) and very good yields (up to 99%).
- Asymmetric catalysis,
- Intramolecular aza-Michael reaction,
- Primary amine,
- Five-and six-membered heterocycles,
- Pyrrolidine and piperidine,
- Enantioselective organocatalytic
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