Cyanosilylation of Ketones Catalyzed by Quaternary Ammonium Salt and N-Oxide

Hui Zhou; Fu-Xue Chen; Bo Qin; Xiaoming Feng; Guolin Zhang

doi:10.1055/s-2004-820045

LETTER

Cyanosilylation of Ketones Catalyzed by Quaternary Ammonium Salt and N-Oxide

Hui Zhou^a, Fu-Xue Chen^a, Bo Qin^a, Xiaoming Feng*^a, Guolin Zhang^b
^a Key Laboratory of Green Chemistry & Technology (Sichuan University), Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China
Fax: +86(28)85418249; e-Mail: xmfeng@scu.edu.cn;
^b Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, P. R. China

Abstract

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Abstract

Dibenzyldimethyl ammonium bromide and triethanolamine N-oxide catalyze the formation of cyanohydrin trimethylsilyl ethers of ketones in 80-99% yield.

Key words

cyanohydrins - ketones - N-oxides - quaternary ammonium salts - organocatalysis

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References

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Typical Procedure: To a mixture of ketone (1.1 mmol), dibenzyldimethyl ammonium bromide (0.027 mmol) and triethanolamine N-oxide (0.027 mmol) in CH₂Cl₂ (0.5 mL) was added trimethylsilyl cyanide (2.2 mmol, 2 equiv.) at r.t. The reaction was monitored by TLC, and after the reaction period described in Table [4] , the reaction mixture was concentrated under reduced pressure and purified by silica gel column to give the pure product with Et₂O-petroleum ether (1:100) as the eluent.