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

Nouch, Ryan and Cini, Melchior and Magre, Marc and Abid, Mohammed and Diéguez, Monserrat and Pàmies, Oscar and 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

[img] PDF - Repository staff only until 30 October 2018. - Requires a PDF viewer such as GSview, Xpdf or Adobe Acrobat Reader
Download (529kB)

Abstract

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.

Item Type: Article
Schools/Departments: University of Nottingham, UK > Faculty of Science > School of Chemistry
Identification Number: 10.1002/chem.201704247
Depositing User: Smith, Ruth
Date Deposited: 01 Nov 2017 11:16
Last Modified: 01 Nov 2017 11:24
URI: http://eprints.nottingham.ac.uk/id/eprint/47715

Actions (Archive Staff Only)

Edit View Edit View