Tetrahedron p. 967 - 974 (1983)
Update date:2022-08-29
Topics:
Utimoto, Kiitiro
Wakabayashi, Yukio
Horiie,Takafumi
Inoue, Masaharu
Shishiyama, Yuho
et al.
Cyanotrimethylsilane adds to some α,β-unsaturated ketones in conjugate manner under the catalytic action of Lewis acids such as triethylaluminium, aluminium chloride, and SnCl2.Hydrolysis of the products gives β-cyano ketones which are identical to the hydrocyanated products of the starting enones.The title silicon reagent reacts with acetals and orthoesters under the catalytic action of SnCl2 or BF3*OEt2 affording 2-alkoxy- and 2,2-dialkoxyalkanenitriles.Application of the reaction to O-protected β-D-ribofuranoses gives selectively β-D-ribofuranosyl cyanide in excellent yield.
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