Organocatalytic C(sp3)-H Functionalization of 5-Methyl-2,3-dihydrofuran Derivatives with Trifluoropyruvates via a Sequential exo-Tautomerization/Carbonyl-Ene Process

Yao-Bin Shen; Shuai-Shuai Li; Yun-Ming Sun; Liping Yu; Zhi-Hui Hao; Qing Liu; Jian Xiao

doi:10.1021/acs.joc.8b03170

Organocatalytic C(sp³)-H Functionalization of 5-Methyl-2,3-dihydrofuran Derivatives with Trifluoropyruvates via a Sequential exo-Tautomerization/Carbonyl-Ene Process

J Org Chem. 2019 Mar 1;84(5):2779-2785. doi: 10.1021/acs.joc.8b03170. Epub 2019 Feb 12.

Authors

Yao-Bin Shen¹, Shuai-Shuai Li¹, Yun-Ming Sun¹, Liping Yu², Zhi-Hui Hao¹, Qing Liu³, Jian Xiao^{1

4}

Affiliations

¹ College of Chemistry and Pharmaceutical Sciences , Qingdao Agricultural University , Qingdao 266109 , China.
² College of Landscape Architecture and Forestry , Qingdao Agricultural University , Qingdao 266109 , China.
³ College of Chemical and Environmental Engineering , Shandong University of Science and Technology , Qingdao 266590 , China.
⁴ College of Marine Science and Engineering , Qingdao Agricultural University , Qingdao 266109 , China.

PMID: 30676022
DOI: 10.1021/acs.joc.8b03170

Abstract

An organocatalytic C(sp³)-H functionalization of 5-methyl-2,3-dihydrofuran derivatives with trifluoropyruvates was achieved via a sequential exo-tautomerization/carbonyl-ene process, providing the biologically important CF₃-substituted 2,3-dihydrofurans in high yields. This method featured mild metal-free conditions, good chemoselectivity, and easy scalability.