CYANOTRIMETHYLSILANE AS A VERSATILE REAGENT FOR INTRODUCING CYANIDE FUNCTIONALITY

Article abstract of DOI:10.1016/S0040-4020(01)88595-1

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.