Convenient and easy access to 2-hydroxycyclopent-2-enones from acylcyanohydrins. Issue 33 (16th August 2019)

• Record Type: Journal Article
• Authors: Pantin, Mathilde; Bodinier, Florent; Saillour, Jordan; Youssouf, Yassine M.; Boeda, Fabien; Pearson-Long, Morwenna S.M.; Bertus, Philippe
• Is Part Of: Tetrahedron. Volume 75:Issue 33(2019)
• Page Start: 4657
• Page End: 4662
• Publication Date: 2019-08-16
• Subjects: Nitriles -- Grignard reagents -- Titanium -- Cyclopentenones; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2019.07.010
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A convenient access to 2-hydroxycyclopentenones was designed from acylcyanohydrins, by using titanacyclopropane complexes as nucleophilic partners and an intramolecular aldol condensation in basic conditions. The development of a one-pot procedure allows a step- and atom-economic process, and the use of Grignard reagents other than ethylmagnesium bromide provided valuable 3, 4-disubstituted 2-hydroxycyclopentenones. The utility of the hydroxy group was illustrated by further functionalization of the α-position using palladium-mediated cross-coupling reactions. Graphical abstract: Image 1 Highlights: Original substituted 2-hydroxycyclopentenones.. Titanacyclopropane complexes.