Volume 38, Issue 8 pp. 807-811
Concise Report

Sequential Ir-Catalyzed Allylation/2-aza-Cope Rearrangement Strategy for the Construction of Chiral Homoallylic Amines

Ruo-Qing Wang

Ruo-Qing Wang

Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072 China

These authors contributed equally to this work.

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Chong Shen

Chong Shen

Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072 China

These authors contributed equally to this work.

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Xiang Cheng

Xiang Cheng

Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072 China

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Zuo-Fei Wang

Zuo-Fei Wang

Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072 China

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Hai-Yan Tao

Hai-Yan Tao

Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072 China

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Xiu-Qin Dong

Corresponding Author

Xiu-Qin Dong

Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072 China

E-mail: [email protected]; [email protected]Search for more papers by this author
Chun-Jiang Wang

Corresponding Author

Chun-Jiang Wang

Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072 China

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 230021 China

E-mail: [email protected]; [email protected]Search for more papers by this author
First published: 14 March 2020
Citations: 15

Dedicated to the 70th Anniversary of Shanghai Institute of Organic Chemistry.

Summary of main observation and conclusion

Sequential Ir-catalyzed asymmetric allylation/2-aza-Cope rearrangement of arylidene aminomalonates with allylic carbonates was successfully developed, and a variety of enantioenriched homoallylic amine derivatives were obtained in high yields with good chirality transfer and excellent E/Z-geometry control (up to 99% yield, 96% ee). Compared with previous dual catalytic system established for this transformation, the current mono metal catalytic system provides a simpler and more practical protocol employing the readily available starting materials.

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