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Cyclobutenones and Benzocyclobutenones: Versatile Synthons in Organic Synthesis
Author(s) -
Chen Penghao,
Dong Guangbin
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201603382
Subject(s) - synthon , nucleophile , electrophile , chemistry , enone , ring (chemistry) , reactivity (psychology) , cyclobutanes , organic synthesis , double bond , ring strain , catalysis , cycloaddition , organic chemistry , combinatorial chemistry , stereochemistry , medicine , alternative medicine , pathology
Cyclobutenones, four‐membered ketones bearing an unsaturated carbon–carbon double bond, and their structural sibling benzocyclobutenones, possess unique reactivity. Owing to their inherent high ring strain, such structures readily undergo ring opening under a variety of conditions, including thermolysis, photolysis, and transition metal catalysis, to afford reactive intermediates that can be trapped with nucleophiles, dienophiles, and unsaturated bonds. Their electron‐deficient enone moieties are good electrophiles for facile nucleophilic addition. Such properties render cyclobutenones versatile synthons, serving as excellent coupling partners in a vast array of synthetically valuable transformations.