Copper-catalyzed asymmetric silylative cyclization of cyclohexadienone-containing 1, 6-enynes. Issue 12 (22nd March 2019)

• Record Type: Journal Article
• Authors: He, Cheng-Yu; Xie, Li-Bo; Ding, Rui; Tian, Ping; Lin, Guo-Qiang
• Is Part Of: Tetrahedron. Volume 75:Issue 12(2019)
• Page Start: 1682
• Page End: 1688
• Publication Date: 2019-03-22
• Subjects: Copper catalysis -- 1, 6-Enynes -- Silylative cyclization -- cis-Hydrobenzofuran; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.12.002
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: The first copper-catalyzed asymmetric silylative cyclization of cyclohexadienone-containing 1, 6-enynes has been accomplished through a tandem process: regioselective silylcupration of terminal unactivated alkynes and subsequently enantioselective conjugate addition to cyclohexadienones. This reaction proceeded smoothly to afford the cis -hydrobenzofuran and cis -hydroindole frameworks bearing two consecutive chiral carbon centers in high to excellent yields and moderate enantioselectivities. Additionally, the cyclization products could be readily subjected to several transformations for elaborating synthetic utilities. Graphical abstract: Image 1