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Cyclobutenones and Benzocyclobutenones: Versatile Synthons in Organic Synthesis

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 51, Pages 18290-18315

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201603382

Keywords

cycloaddition; electrocyclic reactions; enones; homogeneous catalysis; strained molecules

Funding

  1. NIGMS [R01GM109054]
  2. Welch Foundation [F 1781]

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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.

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