The nucleophilic addition (alkylation/arylation) of lithium tetraorganozincate species (R4ZnLi2) to coumarin derivatives takes place cleanly, with a short reaction time (30 min) and with high chemoselectivity, when working under mild conditions (0 °C) and with no additional solvents. Particularly remarkable is the diastereoselectivity of the reaction (up to 96:4), after trapping the resulting intermediates with external electrophiles. The stereochemistry of the major trisubstituted stereoisomer was assigned by combining 2D NOESY experiments with DFT calculations.
Highly chemoselective conjugate addition of lithium tetraorganozincates to coumarin derivatives and functionalization with electrophiles
Marzia Dell’Aera;Filippo Maria Perna;Paola Vitale;Antonio Salomone;Vito Capriati
2023-01-01
Abstract
The nucleophilic addition (alkylation/arylation) of lithium tetraorganozincate species (R4ZnLi2) to coumarin derivatives takes place cleanly, with a short reaction time (30 min) and with high chemoselectivity, when working under mild conditions (0 °C) and with no additional solvents. Particularly remarkable is the diastereoselectivity of the reaction (up to 96:4), after trapping the resulting intermediates with external electrophiles. The stereochemistry of the major trisubstituted stereoisomer was assigned by combining 2D NOESY experiments with DFT calculations.File in questo prodotto:
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