Cesium Effect:  High Chemoselectivity in Direct N-Alkylation of Amines

A novel method for the mono-N-alkylation of primary amines, diamines, and polyamines was developed using cesium bases in order to prepare secondary amines efficiently. A cesium base not only promoted alkylation of primary amines but also suppressed overalkylations of the produced secondary amines. V...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-02, Vol.67 (3), p.674-683
Main Authors: Salvatore, Ralph Nicholas, Nagle, Advait S., Jung, Kyung Woon
Format: Article
Language:English
Subjects:
Aliphatic compounds
Alkylation
Amines - chemistry
Cesium - chemistry
Chemistry
Exact sciences and technology
Magnetic Resonance Spectroscopy
Molecular Mimicry
Organic chemistry
Peptides - chemistry
Preparations and properties
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Summary:A novel method for the mono-N-alkylation of primary amines, diamines, and polyamines was developed using cesium bases in order to prepare secondary amines efficiently. A cesium base not only promoted alkylation of primary amines but also suppressed overalkylations of the produced secondary amines. Various amines, alkyl bromides, and alkyl sulfonates were examined, and the results demonstrated this methodology was highly chemoselective to favor mono-N-alkylation over dialkylation. In particular, use of either sterically demanding substrates or amino acid derivatives afforded the secondary amines exclusively, offering wide applications in peptidomimetic syntheses.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo010643c