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Addition of trimethylsilyl cyanide to α-substituted ketones: Catalyst efficiency

✍ Scribed by W.J. Greenlee; D.G. Hangauer

Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
104 KB
Volume
24
Category
Article
ISSN
0040-4039

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✦ Synopsis

Addition of trimethylsilyl cyanide to o-substituted ketones is often slow and incomplete when catalyzed by zinc iodide. Use of potassium cyanide/la-crown-6 complex as catalyst is a superior method, providing high yields of adducts.

The addition of trimethylsilyl cyanide (TMSCN) to carbonyl compounds is a convenient route for preparation of the corresponding cyanohydrin trimethylsilyl ethers.

1 These serve not only as protected analogs of aldehydes and ketones but also as intermediates for synthesis of cyanohydrins, 2 cc-hydroxyamides, 3 a,&unsaturated nitriles, 4 and B-aminoalcohols.

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The catalytic addition of trimethylsilyl cyanide (TMSCN) to a large variety of hetero-substituted ketones promoted by anhydrous InBr 3 has been studied. The low catalytic loading (0.1-1 mol%) and the mild experimental conditions required represent the key features of this novel catalytic system.

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AbstractÐThe 1,2-and 1.4-addition reactions of trimethylsilyl cyanide to alkyl vinyl ketones were studied. Regioselectivity of this reaction depends on the structure of alkyl vinyl ketones, the reaction temperature and the nature of catalyst. The presence of alkoxy group in b-position of a,b-enone i