Cyclobutenones and Benzocyclobutenones: Versatile Synthons in Organic Synthesis.
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.
Department of Chemistry, University of Texas at Austin, 100 East 24th street, Austin, TX, 78712, USA.
Peng-Hao
PH
Chen
Department of Chemistry, University of Texas at Austin, 100 East 24th street, Austin, TX, 78712, USA.|Department of Chemistry, University of Chicago, Chicago, Illinois, 60637, USA.
Guangbin
http://orcid.org/0000-0003-1331-6015
G
Dong
cycloaddition; electrocyclic reactions; enones; homogeneous catalysis; strained molecules