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Ni-Catalyzed 1,5-Sigmatropic Ester Shift on Cyclopentadiene Rings: Regioselective Conversion of 5,5-Disubstituted Cyclopentadienes to CH-Cyclopentadienes.

作者信息

Bi Hongyan, Chu Jiaxin, Zhao Xiao-Li, Wang Sunewang R

机构信息

Chang-Kung Chuang Institute, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200241, China.

Shanghai Key Laboratory of Green Chemistry & Chemical Processes, East China Normal University, Shanghai 200062, China.

出版信息

Org Lett. 2024 Feb 23;26(7):1437-1441. doi: 10.1021/acs.orglett.4c00062. Epub 2024 Feb 12.

DOI:10.1021/acs.orglett.4c00062
PMID:38345600
Abstract

Described herein is a nickel(II)-catalyzed regioselective rearrangement of 5,5-disubstituted cyclopentadienes to fully functionalized CH-cyclopentadienes via successive 1,5-sigmatropic shifts of the ester group on the quaternary carbon and hydrogen under mild basic conditions. The obtained CH-cyclopentadienes were also readily applied in the preparation of highly functionalized dibenzo[,]azulene derivatives in two steps.

摘要

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