Cyanosilanes reactions with

Cyclohexanone allowed to react with an equimolar amount of trimethylsilyl cyanide in the presence of a trace of zinc iodide product. Y 94%. - The 0X0 compds. may be readily regenerated in dil. aq. acid or base. F. e., also from aldehydes, s. D. A. Evans, L. K. Truesdale, and G. L. Carroll, Chem. Commun. 1973, 55 with AlClg cf. W. Lidy and W. Sundermeyer, B. 106, 587 (1973) f. reactions with cyanosilanes cf. Tetrah. Let. 1973, 1449 preferential protection of carbonyl groups in quinones, f. catalysts, cf. Am. Soc. 95, 5822 (1973). 

Reactions with cyanosilanes a-Siloxynitriles from oxo compds. 

Cyanosilylations of carbon-oxygen and carbon-nitrogen double bonds with cyanosilanes are very important synthetic reactions since the products, cyanohydrin silyl ethers and a-amino nitriles, serve as synthetic intermediates for a variety of natural products. A number of studies on these subjects have been reported in the last decade however, this review does not deal with carbonyl and imine cyanosilylations due to the availability of recent reviews and limited... 

The Ni-catalyzed reaction of 2-bromo-l,6-heptadienes with cyanosilanes affords cyclic and open chain adducts (Scheme 10.245) [669]. TMSCN and El.SiCN are available for this reaction whereas bulky cyanosilanes such as TBSCN and i-PtsSiCN result in sluggish or incomplete reactions leading to predominant formation of fhe open chain adducts. The product ratio is strongly affected by the substitution pattern of fhe substrate. 

Near total 1,2- and 1, 3-asymmetric induction was observed in reactions of a- and -alkoxyacyl cyanides respectively, with the tertiary cyanohydrins to obtained being configurationally stable. Secondary cyanohydrins were obtained after addition of cyanosilanes to the acyl cyanides under similar conditions but with only partial asymmetric induction. The potential application of these methods to the synthesis of carbohydrates was noted. 

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