Cargando…

Boosting the Enantioselectivity of Conjugate Borylation of α,β‐Disubstituted Cyclobutenones with Monooxides of Chiral C (2)‐Symmetric Bis(phosphine) Ligands

Chiral bis(phosphine) monooxides (BPMOs) derived from C (2)‐symmetric bis(phosphines) have been found to induce superior levels of enantioselection in copper‐catalyzed conjugate borylation of α,β‐disubstituted cyclobutenones. More precisely, enantiomeric excesses as well as chemical yields are excee...

Descripción completa

Detalles Bibliográficos
Autores principales: Cui, Ming, Zhao, Zhi‐Yuan, Oestreich, Martin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9804767/
https://www.ncbi.nlm.nih.gov/pubmed/35816363
http://dx.doi.org/10.1002/chem.202202163
_version_ 1784862186200367104
author Cui, Ming
Zhao, Zhi‐Yuan
Oestreich, Martin
author_facet Cui, Ming
Zhao, Zhi‐Yuan
Oestreich, Martin
author_sort Cui, Ming
collection PubMed
description Chiral bis(phosphine) monooxides (BPMOs) derived from C (2)‐symmetric bis(phosphines) have been found to induce superior levels of enantioselection in copper‐catalyzed conjugate borylation of α,β‐disubstituted cyclobutenones. More precisely, enantiomeric excesses as well as chemical yields are exceedingly high with (R,R)‐Bozphos as the chiral ligand while these values are low with parent (R,R)‐Me‐Duphos. A similar yet less pronounced effect was seen in the corresponding 1,6‐addition to para‐quinone methides.
format Online
Article
Text
id pubmed-9804767
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-98047672023-01-06 Boosting the Enantioselectivity of Conjugate Borylation of α,β‐Disubstituted Cyclobutenones with Monooxides of Chiral C (2)‐Symmetric Bis(phosphine) Ligands Cui, Ming Zhao, Zhi‐Yuan Oestreich, Martin Chemistry Research Articles Chiral bis(phosphine) monooxides (BPMOs) derived from C (2)‐symmetric bis(phosphines) have been found to induce superior levels of enantioselection in copper‐catalyzed conjugate borylation of α,β‐disubstituted cyclobutenones. More precisely, enantiomeric excesses as well as chemical yields are exceedingly high with (R,R)‐Bozphos as the chiral ligand while these values are low with parent (R,R)‐Me‐Duphos. A similar yet less pronounced effect was seen in the corresponding 1,6‐addition to para‐quinone methides. John Wiley and Sons Inc. 2022-09-01 2022-11-07 /pmc/articles/PMC9804767/ /pubmed/35816363 http://dx.doi.org/10.1002/chem.202202163 Text en © 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Articles
Cui, Ming
Zhao, Zhi‐Yuan
Oestreich, Martin
Boosting the Enantioselectivity of Conjugate Borylation of α,β‐Disubstituted Cyclobutenones with Monooxides of Chiral C (2)‐Symmetric Bis(phosphine) Ligands
title Boosting the Enantioselectivity of Conjugate Borylation of α,β‐Disubstituted Cyclobutenones with Monooxides of Chiral C (2)‐Symmetric Bis(phosphine) Ligands
title_full Boosting the Enantioselectivity of Conjugate Borylation of α,β‐Disubstituted Cyclobutenones with Monooxides of Chiral C (2)‐Symmetric Bis(phosphine) Ligands
title_fullStr Boosting the Enantioselectivity of Conjugate Borylation of α,β‐Disubstituted Cyclobutenones with Monooxides of Chiral C (2)‐Symmetric Bis(phosphine) Ligands
title_full_unstemmed Boosting the Enantioselectivity of Conjugate Borylation of α,β‐Disubstituted Cyclobutenones with Monooxides of Chiral C (2)‐Symmetric Bis(phosphine) Ligands
title_short Boosting the Enantioselectivity of Conjugate Borylation of α,β‐Disubstituted Cyclobutenones with Monooxides of Chiral C (2)‐Symmetric Bis(phosphine) Ligands
title_sort boosting the enantioselectivity of conjugate borylation of α,β‐disubstituted cyclobutenones with monooxides of chiral c (2)‐symmetric bis(phosphine) ligands
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9804767/
https://www.ncbi.nlm.nih.gov/pubmed/35816363
http://dx.doi.org/10.1002/chem.202202163
work_keys_str_mv AT cuiming boostingtheenantioselectivityofconjugateborylationofabdisubstitutedcyclobutenoneswithmonooxidesofchiralc2symmetricbisphosphineligands
AT zhaozhiyuan boostingtheenantioselectivityofconjugateborylationofabdisubstitutedcyclobutenoneswithmonooxidesofchiralc2symmetricbisphosphineligands
AT oestreichmartin boostingtheenantioselectivityofconjugateborylationofabdisubstitutedcyclobutenoneswithmonooxidesofchiralc2symmetricbisphosphineligands