Zinc‐Catalyzed Enantioselective [3+2] Cycloaddition of Azomethine Ylides Using Planar Chiral [2.2]Paracyclophane‐Imidazoline N,O‐ligands

We present a facile synthetic route toward a novel series of imidazolinyl‐[2.2]paracyclophanol (UCD‐Imphanol) ligands possessing central and planar chirality. Both sets of diastereomeric ligands were successfully purified by column chromatography. The preliminary application of this family of ligand...

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Detalles Bibliográficos
Autores principales: Kumar, Sundaravel Vivek, Guiry, Patrick J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Research Articles
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9543521/
https://www.ncbi.nlm.nih.gov/pubmed/35603757
http://dx.doi.org/10.1002/anie.202205516
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author Kumar, Sundaravel Vivek
Guiry, Patrick J.
author_facet Kumar, Sundaravel Vivek
Guiry, Patrick J.
author_sort Kumar, Sundaravel Vivek
collection PubMed
description We present a facile synthetic route toward a novel series of imidazolinyl‐[2.2]paracyclophanol (UCD‐Imphanol) ligands possessing central and planar chirality. Both sets of diastereomeric ligands were successfully purified by column chromatography. The preliminary application of this family of ligands showed excellent activities in the asymmetric Zn‐catalyzed azomethine ylide cycloaddition. Enantioenriched pyrrolidines, in a substrate scope of 20 examples, were accessed in high levels of endo/exo ratios (up to >99/1) and enantioselectivities (up to >99 % ee) with excellent yields (up to 99 %) by using (S,S,S (P))‐UCD‐Imphanol/(S,S,R (P))‐UCD‐Imphanol, respectively.
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spelling pubmed-95435212022-10-14 Zinc‐Catalyzed Enantioselective [3+2] Cycloaddition of Azomethine Ylides Using Planar Chiral [2.2]Paracyclophane‐Imidazoline N,O‐ligands Kumar, Sundaravel Vivek Guiry, Patrick J. Angew Chem Int Ed Engl Research Articles We present a facile synthetic route toward a novel series of imidazolinyl‐[2.2]paracyclophanol (UCD‐Imphanol) ligands possessing central and planar chirality. Both sets of diastereomeric ligands were successfully purified by column chromatography. The preliminary application of this family of ligands showed excellent activities in the asymmetric Zn‐catalyzed azomethine ylide cycloaddition. Enantioenriched pyrrolidines, in a substrate scope of 20 examples, were accessed in high levels of endo/exo ratios (up to >99/1) and enantioselectivities (up to >99 % ee) with excellent yields (up to 99 %) by using (S,S,S (P))‐UCD‐Imphanol/(S,S,R (P))‐UCD‐Imphanol, respectively. John Wiley and Sons Inc. 2022-06-09 2022-08-15 /pmc/articles/PMC9543521/ /pubmed/35603757 http://dx.doi.org/10.1002/anie.202205516 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Research Articles
Kumar, Sundaravel Vivek
Guiry, Patrick J.
Zinc‐Catalyzed Enantioselective [3+2] Cycloaddition of Azomethine Ylides Using Planar Chiral [2.2]Paracyclophane‐Imidazoline N,O‐ligands
title Zinc‐Catalyzed Enantioselective [3+2] Cycloaddition of Azomethine Ylides Using Planar Chiral [2.2]Paracyclophane‐Imidazoline N,O‐ligands
title_full Zinc‐Catalyzed Enantioselective [3+2] Cycloaddition of Azomethine Ylides Using Planar Chiral [2.2]Paracyclophane‐Imidazoline N,O‐ligands
title_fullStr Zinc‐Catalyzed Enantioselective [3+2] Cycloaddition of Azomethine Ylides Using Planar Chiral [2.2]Paracyclophane‐Imidazoline N,O‐ligands
title_full_unstemmed Zinc‐Catalyzed Enantioselective [3+2] Cycloaddition of Azomethine Ylides Using Planar Chiral [2.2]Paracyclophane‐Imidazoline N,O‐ligands
title_short Zinc‐Catalyzed Enantioselective [3+2] Cycloaddition of Azomethine Ylides Using Planar Chiral [2.2]Paracyclophane‐Imidazoline N,O‐ligands
title_sort zinc‐catalyzed enantioselective [3+2] cycloaddition of azomethine ylides using planar chiral [2.2]paracyclophane‐imidazoline n,o‐ligands
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9543521/
https://www.ncbi.nlm.nih.gov/pubmed/35603757
http://dx.doi.org/10.1002/anie.202205516
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AT guirypatrickj zinccatalyzedenantioselective32cycloadditionofazomethineylidesusingplanarchiral22paracyclophaneimidazolinenoligands

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