Visible-Light-Driven Dearomatization Reaction toward the Formation of Spiro[4.5]deca-1,6,9-trien-8-ones

Wuheng Dong; Yao Yuan; Xiaomin Xie; Zhaoguo Zhang

doi:10.1021/acs.orglett.9b04283

Visible-Light-Driven Dearomatization Reaction toward the Formation of Spiro[4.5]deca-1,6,9-trien-8-ones

Org Lett. 2020 Jan 17;22(2):528-532. doi: 10.1021/acs.orglett.9b04283. Epub 2020 Jan 7.

Authors

Wuheng Dong^{1

2}, Yao Yuan², Xiaomin Xie², Zhaoguo Zhang^{2

3}

Affiliations

¹ Medicine Center , Guangxi University of Science and Technology , Liuzhou , Guangxi 545006 , China.
² Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering , Shanghai Jiao Tong University , 800 Dongchuan Road , Shanghai 200240 , China.
³ Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , China.

PMID: 31908167
DOI: 10.1021/acs.orglett.9b04283

Abstract

A visible-light-driven regioselective dearomative cyclization between 2-benzyl-2-bromomalonate and alkynes under mild conditions leading to the formation of spiro[4,5]decanes has been developed. In the presence of H₂O, a variety of 2-benzyl-2-bromomalonates smoothly undergo 5-exo-dig radical dearomative cyclization with alkynes to afford the corresponding spiro[4,5]decanes in moderate to good yield in a step-economical manner under oxidant-free conditions.