Convenient and easy access to 2-hydroxycyclopent-2-enones from acylcyanohydrins

Mathilde Pantin (1) , Florent Bodinier (1) , Jordan Saillour (1) , Yassine Youssouf (1) , Fabien Boeda (1) , Morwenna S.M. Pearson-Long (1) , Philippe Bertus (1)

1 IMMM - Institut des Molécules et Matériaux du Mans

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.

Mots clés: Nitriles; Grignard reagents; Titanium; Cyclopentenones

Domaines: Chimie

Mathilde Pantin, Florent Bodinier, Jordan Saillour, Yassine Youssouf, Fabien Boeda, et al.. Convenient and easy access to 2-hydroxycyclopent-2-enones from acylcyanohydrins. Tetrahedron, 2019, 75 (33), pp.4657-4662. ⟨10.1016/j.tet.2019.07.010⟩. ⟨hal-02312591⟩