In:
Angewandte Chemie, Wiley, Vol. 127, No. 49 ( 2015-12), p. 15028-15031
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.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.v127.49
DOI:
10.1002/ange.201508125
Language:
German
Publisher:
Wiley
Publication Date:
2015
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