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Synfacts 2006(11): 1180-1180
DOI: 10.1055/s-2006-949398
DOI: 10.1055/s-2006-949398
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York
An Immobilized Organocatalyst for Cyanosilylation
K. Yamaguchi, T. Imago, Y. Ogasawara, J. Kasai, M. Kotani, N. Mizuno*
The University of Tokyo and Science and Technology Agency, Saitama, Japan
Further Information
Publication History
Publication Date:
24 October 2006 (online)
Significance
The immobilized organocatalyst 1-OH/SiO2 was synthesized and found to be highly effective for the cyanosilylation of various carbonyl compounds with trimethylsilyl cyanide. Thus, N-alkylation of 3-(2-imidazolin-1-yl)propyltriethoxysilane with 1-chlorooctane gave N-octyldihydroimidazolium chloride (1-Cl). Compound 1-Cl/SiO2 was prepared by anchoring 1-Cl covalently onto SiO2. 1-Cl/SiO2 was treated with 28% aqueous NH3 to afford 1-OH/SiO2. Cyanosilylation of various carbonyl compounds with trimethylsilyl cyanide in the presence of 1-OH/SiO2 gave the corresponding cyanohydrins in high yield (17 examples: 81-99% yield).