Cyanide as an efficient and mild catalyst in the aminolysis of esters

T Hoegberg, P Stroem, M Ebner…

Index: Hoegberg, Thomas; Stroem, Peter; Ebner, Michael; Raemsby, Sten Journal of Organic Chemistry, 1987 , vol. 52, # 10 p. 2033 - 2036

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Citation Number: 153

Abstract

Cyanide anion was found to be a versatile catalyst in the aminolysis of nonactivated esters. A comparative study on various catalysts, including (dimethylamino) pyridine, 2- hydroxypyridine, imidazole, and sodium cyanide, in the ammonolysis of ethyl (S)-l-ethyl-2- pyrrolidinecarboxylate(1) in methanol showed sodium cyanide to be the superior catalyst. Furthermore, the reaction was completely stereoconservative; ie, less than 1% ...

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