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2-Cyanoazetidines and Azetidinium Ions: Scaffolds for Molecular Diversity

par Couty, François;Drouillat, Bruno;Evano, Gwilherm ;David, Olivier
Référence European Journal of Organic Chemistry, page (2045-2056)
Publication Publié, 2013

Article révisé par les pairs

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Résumé :

Ring strain in azetidines and azetidinium ions can be efficiently used to promote ring-expansion and ring-opening reactions, and this renders these four-membered heterocycles ideal scaffolds for diversity oriented synthesis. This microreview focuses on 2-cyanoazetidines, which are easily prepared from β-amino alcohols through a ring-closing reaction involving C–C bond formation. The azetidines can be readily expanded to five- to eight-membered nitrogen heterocycles after suitable functionalization and/or activation. Alternatively, N-alkylated derivatives, namely, azetidinium ions, are easily prepared and displayed rich reactivity as new electrophilic building blocks and as sources of nitrogen ylides.