Citation: Chen Chen, Jin Zhou, Jing Jiang, Yang Li, Ting Mao, Cheng Peng, Gu Zhan, Wei Huang. Remote stereocontrol in the (4 + 2) cycloadditions of 1,7-zwitterions: Asymmetric synthesis of multifunctionalized tetrahydroquinoline derivatives[J]. Chinese Chemical Letters, ;2024, 35(1): 108295. doi: 10.1016/j.cclet.2023.108295 shu

Remote stereocontrol in the (4 + 2) cycloadditions of 1,7-zwitterions: Asymmetric synthesis of multifunctionalized tetrahydroquinoline derivatives

State Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China

zhangu@cdutcm.edu.cn

huangwei@cdutcm.edu.cn

Received Date: 26 December 2022
Revised Date: 20 February 2023
Accepted Date: 1 March 2023
Available Online: 5 March 2023

Figures(6)

The scope of stereochemistry recognition usually occurs near the chiral scaffold of a ligand or catalyst. Remote stereocontrol, which can surpass the limits of stereorecognition of remote prochiral centers, has long been a challenging object of great interest in asymmetric catalysis. The current work realized the remote stereocontrol of 1,7-zwitterion intermediates formed from Huang's o-amino aryl MBH carbonates. With simple and easily accessible β-ICD as the bifunctional catalyst, multifunctionalized tetrahydroquinoline derivatives could be synthesized via (4 + 2) cycloadditions with excellent enantioselectivity and diastereoselectivity under mild conditions. The strategy possesses broad substrate scope, and three types of electron-deficient enones are successfully applied. Mechanistic studies disclosed the Lewis base-catalyzed reaction pathway, and H-bonding between the catalyst and enones is crucial for long-range stereocontrol. Scale-up reaction and transformations of the tetrahydroquinoline products demonstrated the potential of this strategy.
- Asymmetric synthesis,
- Tetrahydroquinoline,
- Remote stereocontrol,
- Pyrazolone,
- Lewis base catalysis,
- 1,7-Zwitterion
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