1178513-84-2Relevant articles and documents
Rhodium-Catalyzed 2-Arylphenol-Derived Six-Membered Silacyclization: Straightforward Access toward Dibenzooxasilines and Silicon-Containing Planar Chiral Metallocenes
Zhao, Wen-Tao,Lu, Zhuo-Qun,Zheng, Hanliang,Xue, Xiao-Song,Zhao, Dongbing
, p. 7997 - 8005 (2018)
The C/Si switch strategy has been regarded as a useful and efficient strategy for the discovery of drugs and materials. Thus, development of a methodology to access diverse silacycles is of great significance and in great demand. Among these, C-H bond silylation provides a powerful and straightforward synthetic method to form diverse silacycles in an atom- and step-economical fashion. However, C-H bond silylation has not been used to access any six-membered silicon-bridged π-conjugated scaffolds and enantioselective six-membered C-H silylation has never been presented. Herein, we successfully accessed diverse six-membered π-conjugated dibenzooxasilines via C-H bond silylation and investigated their photophysical properties. Furthermore, we realized enantioselective six-membered C-H siylation to directly afford planar chiral metallocene oxasilolanes with high ee (up to 95% ee). We also demonstrated the synthetic usefulness of dibenzooxasilines and planar chiral metallocene-fused benzooxasilolines as valuable synthetic intermediates via diverse additional transformations. Moreover, six-membered silicon-bridged ladder π-conjugated systems were designed and rapidly constructed by using our methods. The isomerization and silicon effects on molecular geometries and photophysical properties were also evaluated in detail.
Rhodium-catalyzed asymmetric synthesis of silicon-stereogenic dibenzooxasilines via enantioselective transmetalation
Shintani, Ryo,MacIver, Eleanor E.,Tamakuni, Fumiko,Hayashi, Tamio
, p. 16955 - 16958 (2013/01/15)
A rhodium-catalyzed asymmetric synthesis of silicon-stereogenic dibenzooxasilines has been developed. High enantioselectivities have been achieved by employing (S,S)-Me-Duphos as the ligand through " enantioselective transmetalation".
