Chemistry Letters

A Novel Oxidative Transformation of. ALPHA.-Aminonitriles to Amides.

S Yokoshima, T Kubo, H Tokuyama, T Fukuyama

Index: Yokoshima, Satoshi; Kubo, Tetsuji; Tokuyama, Hidetoshi; Fukuyama, Tohru Chemistry Letters, 2002 , # 2 p. 122 - 123

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Citation Number: 8

Abstract

-Aminonitrile is a valuable functional group since it can be used as an acyl anion equivalent in the umpolung synthesis,1 a masked hemiaminal functionality,2 and a precursor of hydro- xylamines.3 In the course of our investigation of total synthesis of gelsemine (1),4 we planned to construct -lactam 4 by conjugate addition of -aminonitrile anion and the subsequent conversion to the lactam. While the expected conjugate addition took place quite smoothly, we ...

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