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Citation: WANG Xiao-Mei, HAN Peng, QIU Xue-Peng, JI Xiang-Ling, GAO Lian-Xun. Synthesis and Characterization of Novel Chiral Organosiliane Derivatives of (S)-BINOL[J]. Chinese Journal of Applied Chemistry, ;2009, 26(1): 42-46. shu

Synthesis and Characterization of Novel Chiral Organosiliane Derivatives of (S)-BINOL

1.
a State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022;
2.
b Graduate School of the Chinese Academy of Sciences, Beijing

Corresponding author: GAO Lian-Xun,
Received Date: 11 December 2007
Available Online: 3 February 2008
Fund Project: 国家自然科学基金资助项目(20674085) (20674085)

Novel chiral triethoxysilane derivatives of(S)-1,1'-bi-2-naphthol(BINOL) substituted at 3 and 3,3' positions of binaphthyl backbone were synthesized conveniently from 2,2'-bis(methoxymethy)-1,1'-binaphthol through three steps,i.e.,carbonylation,reduction and Williamson reaction with 3-chloropropyltriethoxysilane using sodium hydride as a deprotonation reagent.Other chiral triethoxysilane derivatives of(S)-BINOL substituted at 6 and 6,6' positions of binaphthyl backbone were prepared through four steps,including bromization at 6 and 6,6' positions of binaphthyl backbone in addition to the three steps mentioned above.The yields of the four compounds are 84%,62%,82% and 67% respectively.The obtained compounds are stable at room temperature and can be purified by column chromatography.The structures of the final products were characterized by ¹H NMR,¹³C NMR,²⁹Si NMR,IR,ESI-MS and elemental analysis.The silicon atom was confirmed to exist as triethoxysilane in the derivatives by ²⁹Si NMR.
- (S)-BINOL,
- chloropropyltriethoxysilane,
- Williamson reaction,
- structural characterization
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