Chan's diene proved to react with aromatic aldehydes under organocatalytic conditions in presence of a chiral naphthyl-TADDOL derivative to give vinylogous aldols (up to 65% ee) with complete g-selectivity. A further process of hetero-Diels-Alder cycloaddition, leading to chiral pyran-4-one derivatives (up to 60% ee), was favoured by electron-withdrawing substituents on the aromatic ring.
Solvent-free asymmetric vinylogous aldol reaction of Chan's diene with aromatic aldehydes catalyzed by hydrogen bonding
Rosaria Villano;
2009
Abstract
Chan's diene proved to react with aromatic aldehydes under organocatalytic conditions in presence of a chiral naphthyl-TADDOL derivative to give vinylogous aldols (up to 65% ee) with complete g-selectivity. A further process of hetero-Diels-Alder cycloaddition, leading to chiral pyran-4-one derivatives (up to 60% ee), was favoured by electron-withdrawing substituents on the aromatic ring.File in questo prodotto:
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