Reaction of Cyanotrimethylsilane with Oxiranes. Effect of Catalysts or Mediators on Regioselectivity and Ambident Character

Article abstract of DOI:10.1021/jo00382a008

Reaction of cyanotrimethylsilane with oxiranes under the catalytic action of Lewis acids Pd(CN)2, SnCl2, or Me3Ga affords 2-trimethylsiloxy isocyanides by regio- and stereoselective attack of isocyanide on the more substituted carbon.The reaction mediated by aluminium alkoxides gives predominantly 3-trimethylsiloxy nitriles by the selective attack of cyanide on the less substituted carbon.