Synthesis of α‐Hydroxyl Ketones by Metal‐Free C=C Double Bond Cleavage of Enaminones in Aqueous Medium

Author:

Gan Lu12,Liu Yunyun1,Wang Chaoli1,Wan Jie‐Ping13ORCID

Affiliation:

1. National Engineering Research Center for Carbohydrate Synthesis College of Chemistry and Chemical Engineering Jiangxi Normal University Nanchang 330022 China

2. School of Science Nanchang Institute of Technology Nanchang 330029 China

3. International Innovation Center for Forest Chemicals and Materials Nanjing Forestry University Nanjing 310027 China

Abstract

AbstractThe C=C double bond cleavage of enaminones has been accomplished in the presence of methyl sulfonyl azide (MSA) to provide α‐hydroxyl ketones via the reaction with water. The major process of the reactions consists of the formation of a key α‐diazoketone intermediate resulting from the enaminone‐azide annulation, and a successive decomposition. Totally 22 α‐hydroxyl ketones have been synthesized with the yield range from 43 %–83 %.

Funder

National Natural Science Foundation of China

Education Department of Jiangxi Province

Publisher

Wiley

Subject

General Chemistry

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