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Convenient and easy access to 2-hydroxycyclopent-2-enones from acylcyanohydrins |
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| Authors: | Mathilde Pantin Florent Bodinier Jordan Saillour Yassine M. Youssouf Fabien Boeda Morwenna S.M. Pearson-Long Philippe Bertus |
| Affiliation: | Institut des Molécules et Matériaux du Mans (IMMM) – UMR 6283 CNRS, Le Mans Université, Avenue Olivier Messiaen, 72085 Le Mans Cedex 09, France |
| 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. |
| Keywords: | Corresponding author. Tel.: +33 243 833 096 fax: +33 243 833 902. Nitriles Grignard reagents Titanium Cyclopentenones |
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