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. (C) 2018 Elsevier Ltd. All rights reserved.
[1]Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, CAS Key Lab Synthet Chem Nat Subst, 345 Lingling Rd, Shanghai 200032, Peoples R China.
[2]Shanghai Univ Tradit Chinese Med, Innovat Res Inst Tradit Chinese Med, 1200 Cailun Rd, Shanghai 201203, Peoples R China.
(8.0+极速模式)