dc.contributor.author | Huang, J | en_US |
dc.contributor.author | Keenan, T | en_US |
dc.contributor.author | Richard, F | en_US |
dc.contributor.author | Lu, J | en_US |
dc.contributor.author | Jenny, SE | en_US |
dc.contributor.author | Jean, A | en_US |
dc.contributor.author | Arseniyadis, S | en_US |
dc.contributor.author | Leitch, DC | en_US |
dc.date.accessioned | 2024-02-02T14:08:51Z | |
dc.date.available | 2023-12-05 | en_US |
dc.date.issued | 2023-12-05 | en_US |
dc.identifier.uri | https://qmro.qmul.ac.uk/xmlui/handle/123456789/94423 | |
dc.description.abstract | Stereoselective carbon-carbon bond formation via palladium-catalyzed asymmetric allylic alkylation is a crucial strategy to access chiral natural products and active pharmaceutical ingredients. However, catalysts based on the privileged Trost and Pfaltz-Helmchen-Williams PHOX ligands often require high loadings, specific preactivation protocols, and excess chiral ligand. This makes these reactions uneconomical, often unreproducible, and thus unsustainable. Here we report several chiral single-component Pd(0) precatalysts that are active and practically-applicable in a variety of asymmetric allylic alkylation reactions. Despite the decades-long history and widespread use of Trost-type ligands, the precatalysts in this work are the only reported examples of stable, isolable Pd(0) complexes with these ligands. Evaluating these precatalysts across nine asymmetric allylic alkylation reactions reveals high reactivity and selectivity at low Pd loading. Importantly, we also report an unprecedented Pd-catalyzed enantioselective allylation of a hydantoin, achieved on gram scale in high yield and enantioselectivity with only 0.2 mol% catalyst. | en_US |
dc.format.extent | 8058 - ? | en_US |
dc.language | eng | en_US |
dc.relation.ispartof | Nat Commun | en_US |
dc.rights | This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/. | |
dc.title | Chiral, air stable, and reliable Pd(0) precatalysts applicable to asymmetric allylic alkylation chemistry. | en_US |
dc.type | Article | |
dc.rights.holder | © 2023, the Author(s). Published by Nature Research | |
dc.identifier.doi | 10.1038/s41467-023-43512-8 | en_US |
pubs.author-url | https://www.ncbi.nlm.nih.gov/pubmed/38052843 | en_US |
pubs.issue | 1 | en_US |
pubs.notes | Not known | en_US |
pubs.publication-status | Published online | en_US |
pubs.volume | 14 | en_US |
dcterms.dateAccepted | 2023-11-11 | en_US |
rioxxterms.funder | Default funder | en_US |
rioxxterms.identifier.project | Default project | en_US |