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Org Lett. 2004 Aug 5;6(16):2745-8.

Generation and utility of tertiary alpha-aminoorganolithium reagents.

Author information

1
Department 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].

PMID:
15281759
DOI:
10.1021/ol049039p
[Indexed for MEDLINE]

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