Microwave-assisted rapid synthesis of chiral oxazolines

Chiral oxazoline compounds play an extremely important role in asymmetric synthesis and drug discovery. Herein a simpler, greener and more efficient microwave-assisted protocol to rapidly access chiral oxazolines is developed using aryl nitriles or cyano-containing compounds and chiral β-amino alcoh...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2023-03, Vol.21 (11), p.2312-2319
Main Authors: Deng, Haowen, Wang, Jianshe, He, Wei, Ye, Yang, Bai, Renren, Zhang, Xuelei, Ye, Xiang-Yang, Xie, Tian, Hui, Zi
Format: Article
Language:English
Subjects:
Alcohols
Asymmetric synthesis
Atom economy
Catalysts
Cyanides
Environmental protection
Nitriles
Synthesis
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Summary:Chiral oxazoline compounds play an extremely important role in asymmetric synthesis and drug discovery. Herein a simpler, greener and more efficient microwave-assisted protocol to rapidly access chiral oxazolines is developed using aryl nitriles or cyano-containing compounds and chiral β-amino alcohols as starting materials. The reaction proceeds smoothly in the presence of a recoverable heterogeneous catalyst in either concentrated solution or under solvent-free conditions. The advantages of this method include rapidness, convenience, environmental protection, high atom economy, and excellent yields. The protocol should find wider application in the community in the future. A practical protocol involving microwave-assisted cyclization of nitriles and chiral amino indanols has been successfully developed. This enables quick access to chiral oxazolines using a reusable catalyst in a much shorter reaction time.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob02192g