Titanium(IV)-Mediated Ring-Opening/Dehydroxylative Cross-Coupling of Diaryl-Substituted Methanols with Cyclopropanol Derivatives

Abstract

A titanium­(IV)-mediated ring-opening/dehydroxylative cross-coupling of diaryl-substituted methanols with a cyclopropanol derivative was developed. The reactions proceeded efficiently to provide synthetically useful γ,γ-diaryl esters in moderate to good yields, which could be applied to the functionalization of complex molecules derived from bioactive fenofibrate and isoxepac and the synthesis of a precursor of Zoloft.

Harnessing alcohols as sustainable reagents for late-stage functionalisation: synthesis of drugs and bio-inspired compounds

“…Post-product derivatisation resulted medicinally important derivative 253c 0 , which is known as a precursor of Zoloft (Scheme 94). 180 8 Miscellaneous strategies for the application of renewable alcohols 8.1 Remote functionalisation of alcohol using chain-walking strategy One of the most advanced methods to access and functionalise inert C-H bonds in organic synthesis is the chain-walking strategy. This approach allows a metal complex to move along the hydrocarbon chain of the substrate to identify ideal bondforming sites.…”

“…Post-product derivatisation resulted medicinally important derivative 253c′ , which is known as a precursor of Zoloft (Scheme 94). 180…”

Nickel-Catalyzed Carbonylation of Cyclopropanol with Benzyl Bromide for Multisubstituted Cyclopentenone Synthesis

“…Cyclopropanols, easily accessible compounds with intrinsic strain property, are often regarded as an important class of homoenolate equivalent, which can intercept with various electrophiles to forge different functional groups at the β-position of carbonyl compounds . Pioneered by seminal works developed by Nakamura and Kuwajima using siloxycyclopropanes as the homoenolate precursor to participate in diverse addition and cross-coupling reactions mediated by metal salts, numerous ring-opening cross-coupling reactions of cyclopropanol by transition metals have been devoted to access a variety of functionalities at the β-position of ketone moiety. − The existing protocols mainly focus on the intramolecular cycloisomerization or two-component cross-coupling (Scheme i, a). Despite the sustainable advances, the multicomponent reaction of the cyclopropanol is underdeveloped.…”