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

Peng Ying Jiang; Ziyin Guo; San Wu; Shao Hua Xiang; Jun Joelle Wang; Bin Tan

doi:10.3390/catal16060556

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

Peng Ying Jiang
, Ziyin Guo
, San Wu^*
, Shao Hua Xiang
, Jun Joelle Wang^*
, Bin Tan^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

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 S_N2 reactions, directly affording valuable chiral bromo alcohols and chiral oxazolone derivatives in high yields with excellent enantioselectivity.

Original language	English
Article number	556
Number of pages	11
Journal	Catalysts
Volume	16
Issue number	6
DOIs	https://doi.org/10.3390/catal16060556
Publication status	Published - 16 Jun 2026

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SDG 12 Responsible Consumption and Production

User-Defined Keywords

chiral phosphoric acid
asymmetric hydrolysis of 4H-oxazines
α-bromo ketones

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10.3390/catal16060556

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title = "Chiral Phosphoric Acid-Catalyzed Hydrolysis of 4H-Oxazines for Diverse Syntheses",

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.",

keywords = "chiral phosphoric acid, asymmetric hydrolysis of 4H-oxazines, α-bromo ketones",

author = "Jiang, \{Peng Ying\} and Ziyin Guo and San Wu and Xiang, \{Shao Hua\} and Wang, \{Jun Joelle\} and Bin Tan",

note = "Publisher Copyright: {\textcopyright} 2026 by the authors. Licensee MDPI, Basel, Switzerland. Funding Information: This paper was funded by the National Key R\&D Program of China (2022YFA1503700), the National Natural Science Foundation of China (22425011, 22231004, 22271135, 22501129), the Research Grants Council of Hong Kong (SRFS2526-2S02), the Hong Kong Scholars Program (XJ2024-007), the Guangdong Basic and Applied Basic Research Foundation (2024B1515020055), the New Cornerstone Science Foundation through the Xplorer Prize, the Shenzhen Science and Technology Program (KQTD20210811090112004) and High level of special funds (G03050K003).",

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doi = "10.3390/catal16060556",

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T1 - Chiral Phosphoric Acid-Catalyzed Hydrolysis of 4H-Oxazines for Diverse Syntheses

AU - Jiang, Peng Ying

AU - Guo, Ziyin

AU - Wu, San

AU - Xiang, Shao Hua

AU - Wang, Jun Joelle

AU - Tan, Bin

N1 - Publisher Copyright: © 2026 by the authors. Licensee MDPI, Basel, Switzerland. Funding Information: This paper was funded by the National Key R&D Program of China (2022YFA1503700), the National Natural Science Foundation of China (22425011, 22231004, 22271135, 22501129), the Research Grants Council of Hong Kong (SRFS2526-2S02), the Hong Kong Scholars Program (XJ2024-007), the Guangdong Basic and Applied Basic Research Foundation (2024B1515020055), the New Cornerstone Science Foundation through the Xplorer Prize, the Shenzhen Science and Technology Program (KQTD20210811090112004) and High level of special funds (G03050K003).

PY - 2026/6/16

Y1 - 2026/6/16

N2 - 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.

AB - 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.

KW - chiral phosphoric acid

KW - asymmetric hydrolysis of 4H-oxazines

KW - α-bromo ketones

UR - https://www.scopus.com/pages/publications/105042771764

U2 - 10.3390/catal16060556

DO - 10.3390/catal16060556

M3 - Journal article

AN - SCOPUS:105042771764

SN - 2073-4344

VL - 16

JO - Catalysts

JF - Catalysts

IS - 6

M1 - 556

ER -

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

Abstract

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