110966-13-7Relevant articles and documents
Construction of complex cyclobutane building blocks by photosensitized [2 + 2] cycloaddition of vinyl boronate esters
Scholz, Spencer O.,Kidd, Jesse B.,Capaldo, Luca,Flikweert, Niecia E.,Littlefield, Rowan M.,Yoon, Tehshik P.
supporting information, p. 3496 - 3501 (2021/05/10)
Cyclobutyl moieties in drug molecules are rare, and in general, they are minimally substituted and stereochemically simple. Methods to assemble structurally complex cyclobutane building blocks suitable for rapid diversification are thus highly desirable. We report herein a photosensitized [2 + 2] cycloaddition with vinyl boronate esters affording straightforward access to complex, densely functionalized cyclobutane scaffolds. Mechanistic studies suggest an activation mode involving energy transfer to the styrenyl alkene rather than the vinyl boronate ester.
PHOTOCHEMICAL METHODS OF MAKING CYCLOBUTANE BORONATES AND RELATED COMPOUNDS
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Paragraph 0123; 0128, (2019/02/19)
The present technology relates generally cyclobutane boronates, including methods of preparation by exposing a mixture of a compound of Formula I in a solvent and a catalytic amount of a visible light sensitizer to provide a compound of Formula II, stereoisomers thereof, and/or salts of any of the foregoing. The cyclobutane boronate compounds are useful intermediates in the preparation of pharmaceutically active compounds as well as other other useful compounds.
A Sequential Route to Cyclopentenes from 1,6-Enynes and Diazo Ketones through Gold and Rhodium Catalysis
Kale, Balaji S.,Lee, Hsin-Fu,Liu, Rai-Shung
supporting information, p. 402 - 409 (2017/02/10)
This work reports the construction of cyclopentene cores from 1,6-enynes and aryl diazo ketones through two new reaction sequences involving initial gold-catalyzed cyclization of 1,6-enynes with diazo species, followed by rhodium-catalyzed skeletal rearrangement of the resulting 3-cyclopropyl-2-en-1-ones. In most instances the rhodium-catalyzed reactions afforded cyclopentene derivatives whereas several n-alkyl- or ortho-substituted phenyl ketones delivered seven-membered oxacycles. A plausible mechanism provides rationales for these two distinct products. (Figure presented.).