Enantioselective synthesis of 6,6-disubstituted pentafulvenes containing a chiral pendant hydroxy groupTools Nouch, Ryan, Cini, Melchior, Magre, Marc, Abid, Mohammed, Diéguez, Monserrat, Pàmies, Oscar, Woodward, Simon and Lewis, William (2017) Enantioselective synthesis of 6,6-disubstituted pentafulvenes containing a chiral pendant hydroxy group. Chemistry - a European Journal . ISSN 1521-3765 Full text not available from this repository.AbstractSimple enantioselective synthesis of 6,6-disubstituted pentafulvenes bearing chiral pendant hydroxy groups are attained by cascade reactivity using commercially available proline-based organocatalysts. Condensation of cyclopentadiene with the acetyl function of a 1,2-formylacetophenone, followed by cyclization of a resulting fulvene-stabilized carbanion with the formyl group, generates bicyclic chiral alcohols with initial er values up to 94:6. Exceptional enantio-enrichment of the resultant alcohols results upon crystallization – even near racemic samples spontaneously de-racemize. This enables new families of substituted cyclopentadienes that are both enantiomerically and diastereomerically pure to be rapidly attained.
Actions (Archive Staff Only)
|
Tools
Tools
