Experimental and Computational Studies on Interrupted Nazarov Reactions: Exploration of Umpolung Reactivity at the a-Carbon of Cyclopentanones

• Published in: Journal of the American Chemical Society Vol. 136; no. 42; pp. 14903 - 14911
• Main Authors: Wu, Yen-Ku, Dunbar, Christine R., McDonald, Robert, Ferguson, Michael J., West, F. G.
• Format: Journal Article
• Language: English
• Published: WASHINGTON Amer Chemical Soc 22.10.2014
• Subjects: Chemistry; Chemistry, Multidisciplinary; Physical Sciences; Science & Technology; ALLYL CATIONS; CYCLOADDITION REACTIONS; DIELS-ALDER REACTIONS; BOND-FORMING REACTIONS; SOMO CATALYSIS; OXYALLYL CATIONS; STEREOSELECTIVE-SYNTHESIS; CYCLIZATION; QUANTUM-CHEMICAL CHARACTERIZATION; ALLENYL VINYL KETONES

A set of densely substituted, alpha-functionalized cyclopentanones can be generated by a two-component, domino reaction sequence entailing the Nazarov electrocyclization of divinyl ketones and nucleophilic addition of the resulting 2-oxidocyclopentenyl cations by selected trapping modalities. Bypass...