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Efficient Access to Bicyclo[4.3.0]nonanes: Copper‐Catalyzed Asymmetric Silylative Cyclization of Cyclohexadienone‐Tethered Allenes
Author(s) -
He ZhiTao,
Tang XiaoQi,
Xie LiBo,
Cheng Mian,
Tian Ping,
Lin GuoQiang
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201508125
Subject(s) - allene , chemistry , bicyclic molecule , enantioselective synthesis , regioselectivity , vinylsilane , ring (chemistry) , catalysis , tandem , cyclopentanes , stereochemistry , medicinal chemistry , organic chemistry , materials science , composite material
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.