Citation: Tengfei Xuan, Yuan Pan, Zhenyu Shi, Yang Wang. Organocatalytic asymmetric synthesis of oxazolines from N-acylimines[J]. Chinese Chemical Letters, ;2025, 36(6): 110352. doi: 10.1016/j.cclet.2024.110352 shu

Organocatalytic asymmetric synthesis of oxazolines from N-acylimines

Tengfei Xuan ^{a, 1} ,
Yuan Pan ^{a, 1} ,
Zhenyu Shi ^a ,
Yang Wang ^{a, b, *,}

a.
Molecular Synthesis Center & Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
b.
Laboratory for Marine Drugs and Bioproducts, Qingdao Marine Science and Technology Center, Qingdao 266237, China

wangyang@ouc.edu.cn

Received Date: 18 March 2024
Revised Date: 12 August 2024
Accepted Date: 21 August 2024
Available Online: 22 August 2024

Figures(7)

A novel organocatalytic asymmetric approach to oxazoline derivatives that proceeds through Mannich/annulation reaction of N-acylimines with 3-chlorooxindoles is presented. This strategy provides an efficient and convenient method to access enantioenriched oxazolines such as valuable chiral S, N-oxazoline ligand as well as Ferrox ligand in high yields with excellent enantio– and diastereroselectivity. Furthermore, the optically active oxazoline products can be converted to valuable 1, 2-amino alcohols. More importantly, the synthetic utility of this transformation is demonstrated in the expeditious assembly of chiral Phox-type ligand, which shows excellent catalytic activities.
- Organocatalysis,
- Enantioselective,
- Oxazoline,
- N-Acylimine,
- 3-Chlorooxindole
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