Boron-Catalyzed Arylthiooxygenation of N-Allylamides: Synthesis of (Arylsulfanyl)oxazolines

Jipan Yu; Hua Tian; Chang Gao; Haijun Yang; Yuyang Jiang; Hua Fu

doi:10.1055/s-0034-1378948

Synlett, Table of Contents

Synlett 2015; 26(05): 676-680
DOI: 10.1055/s-0034-1378948

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Boron-Catalyzed Arylthiooxygenation of N-Allylamides: Synthesis of (Arylsulfanyl)oxazolines

Jipan Yu

^aKey Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China

,

Hua Tian

^aKey Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China

,

Chang Gao

^aKey Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China

,

Haijun Yang

^aKey Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China

,

Yuyang Jiang

^bKey Laboratory of Chemical Biology (Guangdong Province), Graduate School of Shenzhen, Tsinghua University, Shenzhen 518057, P. R. of China Email: fuhua@mail.tsinghua.edu.cn

,

Hua Fu*

^aKey Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China

^bKey Laboratory of Chemical Biology (Guangdong Province), Graduate School of Shenzhen, Tsinghua University, Shenzhen 518057, P. R. of China Email: fuhua@mail.tsinghua.edu.cn

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Abstract

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Abstract

Oxazoles and aryl sulfides are chemical entities that are found in many natural products and biologically and pharmaceutically active molecules. It is therefore highly desirable to develop an efficient and practical approach to the synthesis of arylsulfanyl-substituted oxazolines. We developed a simple and efficient method for boron-catalyzed sequential arylsulfanylation and oxygenation of N-allylamides. The protocol uses readily available 1-(arylsulfanyl)pyrrolidine-2,5-diones as the arylsulfanylation reagents and inexpensive boron trifluoride etherate as the catalyst; no ligands or additives are required, and it is not necessary to purge the reaction vessel of air. The method therefore provides an efficient and practical strategy for the synthesis of arylsulfanyl-substituted heterocycles.

Key words

oxazoles - sulfurizations - sulfides - oxygenations

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References

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