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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| Format: | Article |
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Wiley-VCH Verlag
2017
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| Online Access: | https://eprints.nottingham.ac.uk/47715/ |
| _version_ | 1848797612068569088 |
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| author | Nouch, Ryan Cini, Melchior Magre, Marc Abid, Mohammed Diéguez, Monserrat Pàmies, Oscar Woodward, Simon Lewis, William |
| author_facet | Nouch, Ryan Cini, Melchior Magre, Marc Abid, Mohammed Diéguez, Monserrat Pàmies, Oscar Woodward, Simon Lewis, William |
| author_sort | Nouch, Ryan |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T20:06:38Z |
| format | Article |
| id | nottingham-47715 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T20:06:38Z |
| publishDate | 2017 |
| publisher | Wiley-VCH Verlag |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-477152020-05-04T19:15:08Z https://eprints.nottingham.ac.uk/47715/ Enantioselective synthesis of 6,6-disubstituted pentafulvenes containing a chiral pendant hydroxy group Nouch, Ryan Cini, Melchior Magre, Marc Abid, Mohammed Diéguez, Monserrat Pàmies, Oscar Woodward, Simon Lewis, William 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. Wiley-VCH Verlag 2017-10-30 Article PeerReviewed 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 http://onlinelibrary.wiley.com/doi/10.1002/chem.201704247/abstract doi:10.1002/chem.201704247 doi:10.1002/chem.201704247 |
| spellingShingle | Nouch, Ryan Cini, Melchior Magre, Marc Abid, Mohammed Diéguez, Monserrat Pàmies, Oscar Woodward, Simon Lewis, William Enantioselective synthesis of 6,6-disubstituted pentafulvenes containing a chiral pendant hydroxy group |
| title | Enantioselective synthesis of 6,6-disubstituted pentafulvenes containing a chiral pendant hydroxy group |
| title_full | Enantioselective synthesis of 6,6-disubstituted pentafulvenes containing a chiral pendant hydroxy group |
| title_fullStr | Enantioselective synthesis of 6,6-disubstituted pentafulvenes containing a chiral pendant hydroxy group |
| title_full_unstemmed | Enantioselective synthesis of 6,6-disubstituted pentafulvenes containing a chiral pendant hydroxy group |
| title_short | Enantioselective synthesis of 6,6-disubstituted pentafulvenes containing a chiral pendant hydroxy group |
| title_sort | enantioselective synthesis of 6,6-disubstituted pentafulvenes containing a chiral pendant hydroxy group |
| url | https://eprints.nottingham.ac.uk/47715/ https://eprints.nottingham.ac.uk/47715/ https://eprints.nottingham.ac.uk/47715/ |