Author, as appears in the article.: Nouch R; Cini M; Magre M; Abid M; Diéguez M; Pàmies O; Woodward S; Lewis W
Department: Química Física i Inorgànica
URV's Author/s: Diéguez Fernández, Montserrat / Pamies Ollé, Oscar
Keywords: Synthetic methods Organocatalysis Fulvenes Carbanions Asymmetric catalysis organocatalysis fulvenes carbanions asymmetric catalysis
Abstract: © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 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.
Thematic Areas: Química Organic chemistry Medicina i Materiais Interdisciplinar General medicine General chemistry Farmacia Engenharias iii Engenharias ii Ciências biológicas iii Ciências biológicas ii Ciências biológicas i Ciências agrárias i Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all) Chemistry Catalysis Biotecnología Biodiversidade Astronomia / física
licence for use: https://creativecommons.org/licenses/by/3.0/es/
ISSN: 15213765
Author's mail: oscar.pamies@urv.cat montserrat.dieguez@urv.cat
Author identifier: 0000-0002-2352-8508 0000-0002-8450-0656
Last page: 17198
Record's date: 2024-09-07
Journal volume: 23
Papper version: info:eu-repo/semantics/submittedVersion
Link to the original source: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/chem.201704247
Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
Papper original source: Chemistry-A European Journal. 23 (68): 17195-17198
APA: Nouch R; Cini M; Magre M; Abid M; Diéguez M; Pàmies O; Woodward S; Lewis W (2017). Enantioselective Synthesis of 6,6-Disubstituted Pentafulvenes Containing a Chiral Pendant Hydroxy Group. Chemistry-A European Journal, 23(68), 17195-17198. DOI: 10.1002/chem.201704247
Article's DOI: 10.1002/chem.201704247
Entity: Universitat Rovira i Virgili
Journal publication year: 2017
First page: 17195
Publication Type: Journal Publications
Repositori URV