Work

Chiral Phosphoric Acid-Catalyzed Hydrolysis of 4H-Oxazines for Diverse Syntheses

Year: 2026

Type: article

Abstract: The use of water as a nucleophile in catalytic asymmetric reactions remains a significant challenge, primarily due to its intrinsically low nucleophilicity and small size, which make precise control over both reactivity and stereoselectivity particularly difficult. To address this issue, we developed a CPA-catalyzed asymmetric hydrolysis system, successfully achieving the efficient and highly stereoselective transformation of 4H-oxazines with water. Under this catalytic system, the initial formation of chiral α-bromo ketones is followed by their in situ conversion through reduction and intramolecular SN2 reactions, directly affording valuable chiral bromo alcohols and chiral oxazolone derivatives in high yields with excellent enantioselectivity.

Source: Catalysts

DOI: 10.3390/catal16060556

Authors: Peng-Ying Jiang, Ziyin Guo, San Wu, Shao-Hua Xiang, Jun (Joelle) Wang, Bin Tan

Institutions: Hong Kong Baptist University, Southern University of Science and Technology

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $2,654

Funders: National Natural Science Foundation of China, Southern University of Science and Technology, National Key Research and Development Program of China, Basic and Applied Basic Research Foundation of Guangdong Province