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Updated: Aug 23, 2026

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
Published on: November 12, 2016
Generation and utility of tertiary alpha-aminoorganolithium reagents
Scott A Wolckenhauer1, Scott D Rychnovsky
1Department of Chemistry, 516 Rowland Hall, University of California-Irvine, Irvine, CA 92697-2025, USA.
Abstract:
A general approach to tertiary alpha-aminoorganolithium reagents by reductive lithiation of alpha-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 alpha-aminoorganocuprate reagents that react with alkyl halide electrophiles and in 1,4-additions with enones. These methods establish a new approach for the synthesis of quaternary centers adjacent to nitrogen. [reaction: see text]
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