Synthesis 2015; 47(05): 641-646
DOI: 10.1055/s-0034-1379636
paper
© Georg Thieme Verlag Stuttgart · New York

Ring-Strain-Driven Catalytic Carbene Formation–Cyclopropanation–Aza-Cope Rearrangement Cascade: A Facile Entry to Fused Dihydroazepines from 1,3-Dienyltriazoles

Hua-Dong Xu*
School of Pharmaceutical Engineering and Life Science, Changzhou University, No. 1 Middle Gehu Rd., Changzhou, Jiangsu Province 213164, P. R. of China   Email: hdxu@cczu.edu.cn   Email: shenmh@cczu.edu.cn
,
Ke Xu
School of Pharmaceutical Engineering and Life Science, Changzhou University, No. 1 Middle Gehu Rd., Changzhou, Jiangsu Province 213164, P. R. of China   Email: hdxu@cczu.edu.cn   Email: shenmh@cczu.edu.cn
,
Hao Zhou
School of Pharmaceutical Engineering and Life Science, Changzhou University, No. 1 Middle Gehu Rd., Changzhou, Jiangsu Province 213164, P. R. of China   Email: hdxu@cczu.edu.cn   Email: shenmh@cczu.edu.cn
,
Zhi-Hong Jia
School of Pharmaceutical Engineering and Life Science, Changzhou University, No. 1 Middle Gehu Rd., Changzhou, Jiangsu Province 213164, P. R. of China   Email: hdxu@cczu.edu.cn   Email: shenmh@cczu.edu.cn
,
Hao Wu
School of Pharmaceutical Engineering and Life Science, Changzhou University, No. 1 Middle Gehu Rd., Changzhou, Jiangsu Province 213164, P. R. of China   Email: hdxu@cczu.edu.cn   Email: shenmh@cczu.edu.cn
,
Xiao-Long Lu
School of Pharmaceutical Engineering and Life Science, Changzhou University, No. 1 Middle Gehu Rd., Changzhou, Jiangsu Province 213164, P. R. of China   Email: hdxu@cczu.edu.cn   Email: shenmh@cczu.edu.cn
,
Mei-Hua Shen*
School of Pharmaceutical Engineering and Life Science, Changzhou University, No. 1 Middle Gehu Rd., Changzhou, Jiangsu Province 213164, P. R. of China   Email: hdxu@cczu.edu.cn   Email: shenmh@cczu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 09 October 2014

Accepted after revision: 14 November 2014

Publication Date:
03 December 2014 (eFirst)

Abstract

A practical method for a facile entry to structurally unique ring-fused dihydroazepine has been developed using 1-sulfonyl-1,3-dienyltriazole as starting materials. Driven by ring strain release of cyclopropyl group, a rhodium-catalyzed α-imino carbenoid formation–cyclopropanation–aza-Cope rearrangement cascade takes place efficiently in a single operation. Substitution effects on yield and diastereoselectivity are also explored.

Supporting Information

 
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