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Issue 16, 2011
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Quaternary centres bearing nitrogen (α-tertiary amines) as products of molecular rearrangements

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Abstract

Quaternary centres bearing a nitrogen substituent (α-tertiary amines and their derivatives) are found in a variety of bioactive molecules but pose a major challenge in synthesis, particularly when enantiomeric purity is required. Approaches comparable to those used for tertiary alcohols are typically hampered by the poor electrophilicity of imines, requiring powerful nucleophiles that may also act as bases. A set of powerful alternative approaches make use of the rearrangement of readily available precursors, often (but not always) with formation of a new tertiary carbon to nitrogen bond. In this Feature Article we review the scope, limitations and specificities of some of these rearrangements in order to illuminate their synthetic potential.

Graphical abstract: Quaternary centres bearing nitrogen (α-tertiary amines) as products of molecular rearrangements

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Publication details

The article was received on 04 Jan 2011, accepted on 01 Feb 2011 and first published on 07 Mar 2011


Article type: Feature Article
DOI: 10.1039/C1CC00049G
Citation: Chem. Commun., 2011,47, 4624-4639
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    Quaternary centres bearing nitrogen (α-tertiary amines) as products of molecular rearrangements

    J. Clayden, M. Donnard, J. Lefranc and D. J. Tetlow, Chem. Commun., 2011, 47, 4624
    DOI: 10.1039/C1CC00049G

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