Asymmetric Gold-Redox Catalysis in Cyclobutanol Ring Expansion toward the Formation of Quaternary Carbon Chiral Center with Hemilabile P,N-Ligand

Investigations of cyclobutanol ring expansion under gold redox catalysis were conducted as a new approach to the stereoselective synthesis of quaternary carbon centers under mild conditions. The chiral hemilabile P,N-ligand Ad-ChetPhos was identified as the optimal system, affording cyclopentanones in moderate to good yields (up to 90%, >30 cases tested) and enantioselectivities of up to 78% ee. This study not only introduces a new method for the asymmetric synthesis of quaternary carbon centers but also demonstrates the feasibility of asymmetric gold redox catalysis under modified basic conditions, providing valuable mechanistic insights for future developments along this pathway.

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Publication Details

Journal
Organic Letters
Published
2025-11-26
DOI
https://doi.org/10.1021/acs.orglett.5c04239
Primary Topic
Catalytic Alkyne Reactions
Type
article
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article

Asymmetric Gold-Redox Catalysis in Cyclobutanol Ring Expansion toward the Formation of Quaternary Carbon Chiral Center with Hemilabile P,N-Ligand

Xiaodong Shi, Xinyu Fu, Kai Zhao, Zhiguang Song et al.
Organic Letters
Catalytic Alkyne Reactions
article

Asymmetric Gold-Redox Catalysis in Cyclobutanol Ring Expansion toward the Formation of Quaternary Carbon Chiral Center with Hemilabile P,N-Ligand

Xiaodong Shi, Xinyu Fu, Kai Zhao, Zhiguang Song, Qi Tang
article en

Abstract

Investigations of cyclobutanol ring expansion under gold redox catalysis were conducted as a new approach to the stereoselective synthesis of quaternary carbon centers under mild conditions. The chiral hemilabile P,N-ligand Ad-ChetPhos was identified as the optimal system, affording cyclopentanones in moderate to good yields (up to 90%, >30 cases tested) and enantioselectivities of up to 78% ee. This study not only introduces a new method for the asymmetric synthesis of quaternary carbon centers but also demonstrates the feasibility of asymmetric gold redox catalysis under modified basic conditions, providing valuable mechanistic insights for future developments along this pathway.

Organic LettersVol. 27(49)
Jilin University (CN), Jilin Medical University (CN), State Key Laboratory of Supramolecular Structure and Materials, University of Maryland, College Park (US)
Openalex Percentile: Top 72%
Catalytic Alkyne Reactions
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