Organic letters

Generation and Utility of Tertiary α-Aminoorganolithium Reagents

SA Wolckenhauer, SD Rychnovsky

Index: Wolckenhauer, Scott A.; Rychnovsky, Scott D. Organic Letters, 2004 , vol. 6, # 16 p. 2745 - 2748

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Citation Number: 19

Abstract

A general approach to tertiary α-aminoorganolithium reagents by reductive lithiation of α- aminonitriles has been developed. This class of organolithium nucleophiles reacts efficiently with carbonyl electrophiles or in intramolecular cyclizations with tethered phosphate leaving groups. Transmetalation can be used to produce α-aminoorganocuprate reagents that react with alkyl halide electrophiles and in 1, 4-additions with enones. These methods establish ...