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- Title
Efficient Access to Bicyclo[4.3.0]nonanes: Copper-Catalyzed Asymmetric Silylative Cyclization of Cyclohexadienone-Tethered Allenes.
- Authors
He, Zhi ‐ Tao; Tang, Xiao ‐ Qi; Xie, Li ‐ Bo; Cheng, Mian; Tian, Ping; Lin, Guo ‐ Qiang
- Abstract
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.
- Subjects
ASYMMETRIC synthesis; ALLENE; RING formation (Chemistry); SILYLATION; CYCLOHEXADIENONES
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 49, p15028
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201508125