Angewandte Chemie - International Edition p. 14815 - 14818 (2015)
Update date:2022-08-04
Topics:
He, Zhi-Tao
Tang, Xiao-Qi
Xie, Li-Bo
Cheng, Mian
Tian, Ping
Lin, Guo-Qiang
The creation of three consecutive chiral carbon centers in one step is achieved using Cu-catalyzed asymmetric silylative cyclization of cyclohexadienone-tethered allenes. Through regioselective β-silylation of the allene and subsequent enantioselective 1,4-addition to cyclohexadienone, this tandem reaction could afford cis-hydrobenzofuran, cis-hydroindole, and cis-hydroindene frameworks with excellent yields (80-98 %) and enantioselectivities (94-98 % ee) bearing vinylsilane and enone substructures. Meanwhile, this mild transformation is generally compatible with a wide range of functional groups, which allows further conversion of the bicyclic products to bridged and tricyclic ring structures. Three in one: Three consecutive chiral carbon centers are formed in one step by a copper-catalyzed asymmetric silylative cyclization of cyclohexadienone-tethered allenes. Thus cis-hydrobenzofuran, cis-hydroindole, and cis-hydroindene frameworks are prepared with exceptional yields (80-98 %) and enantioselectivities (94-98 % ee).
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Doi:10.1246/bcsj.66.2668
(1993)Doi:10.1021/om00059a001
(1992)Doi:10.1016/S0040-4020(01)80759-6
(1994)Doi:10.1002/hlca.19960790602
(1996)Doi:10.1021/ja411869r
(2014)Doi:10.1021/ic402838y
(2014)