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

Jonathan Clayden*, Morgan Donnard, Julien Lefranc, Daniel J. Tetlow

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

114 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)4624-4639
Number of pages16
JournalChemical Communications
Volume47
Issue number16
Early online date7 Mar 2011
DOIs
Publication statusPublished - 28 Apr 2011

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