Enantioselective synthesis of 6,6-disubstituted pentafulvenes containing a chiral pendant hydroxy group

Enantioselective synthesis of 6,6-disubstituted pentafulvenes containing a chiral pendant hydroxy group

Simple 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...

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Bibliographic Details
Main Authors: Nouch, Ryan, Cini, Melchior, Magre, Marc, Abid, Mohammed, Diéguez, Monserrat, Pàmies, Oscar, Woodward, Simon, Lewis, William
Format: Article
Published: Wiley-VCH Verlag 2017
Online Access:https://eprints.nottingham.ac.uk/47715/
Description
Summary:Simple 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.

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