Aminoborohydrides as reducing agents. 1. Sodium (dimethylamino)-and (tert-butylamino) borohydrides as selective reducing agents

RO Hutchins, K Learn, F El-Telbany…

Index: Hutchins, Robert O.; Learn, Keith; El-Telbany, Farag; Stercho, Yuriy P. Journal of Organic Chemistry, 1984 , vol. 49, # 13 p. 2438 - 2443

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Citation Number: 47

Abstract

Replacement of a hydride in borohydride by an electron-donating alkylamine group greatly enhances the reducing ability of the resulting reagents. Thus, sodium (dimethylamino)-and (tert-bu~~ ino) borohydrides (1, NaDMAB, and 2, NaTBAB, respectively) not only reduce aldehydes and ketones to alcohols but also are effective for the conversion of esters to alcohols and primary amides to amines in good to excellent yields. Tertiary amides are ...

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