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Copper-catalyzed asymmetric silylative cyclization of cyclohexadienone-containing 1,6-enynes

Author:
He, Cheng-Yu, Xie, Li-Bo, Ding, Rui, Tian, Ping, Lin, Guo-Qiang
Source:
Tetrahedron 2019 v.75 no.12 pp. 1682-1688
ISSN:
0040-4020
Subject:
alkynes, carbon, chemical reactions, chemical structure, enantioselectivity, regioselectivity
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.
Agid:
6257735