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2‐Cyanoazetidines and Azetidinium Ions: Scaffolds for Molecular Diversity
Author(s) -
Couty François,
Drouillat Bruno,
Evano Gwilherm,
David Olivier
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201685
Subject(s) - chemistry , electrophile , ring (chemistry) , reactivity (psychology) , combinatorial chemistry , nitrogen , alkylation , ion , ring strain , surface modification , stereochemistry , polymer chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
Abstract 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.