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Rational design of a facially coordinating P,N,N ligand for manganese-catalysed enantioselective hydrogenation of cyclic ketones
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dc.contributor.author | Oates, Conor L. | |
dc.contributor.author | Goodfellow, Alister S. | |
dc.contributor.author | Bühl, Michael | |
dc.contributor.author | Clarke, Matthew L. | |
dc.date.accessioned | 2022-12-12T12:30:01Z | |
dc.date.available | 2022-12-12T12:30:01Z | |
dc.date.issued | 2023-01-16 | |
dc.identifier | 282041391 | |
dc.identifier | 180c7513-c368-41f6-a9d1-d932dec451c9 | |
dc.identifier | 85143589526 | |
dc.identifier | 000894253800001 | |
dc.identifier.citation | Oates , C L , Goodfellow , A S , Bühl , M & Clarke , M L 2023 , ' Rational design of a facially coordinating P,N,N ligand for manganese-catalysed enantioselective hydrogenation of cyclic ketones ' , Angewandte Chemie International Edition , vol. 62 , no. 3 , e202212479 . https://doi.org/10.1002/anie.202212479 | en |
dc.identifier.issn | 1433-7851 | |
dc.identifier.other | RIS: urn:FBB90BD720AF8225A9961FE19D6CD40F | |
dc.identifier.other | ORCID: /0000-0002-2444-1244/work/124489944 | |
dc.identifier.other | ORCID: /0000-0002-1095-7143/work/124490010 | |
dc.identifier.uri | https://hdl.handle.net/10023/26573 | |
dc.description | Funding: Authors would like to thank the University of St Andrews, combined with the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT) for financial support [PhD studentship to CO; Grant code: EP/L016419/1], and the EaSI-CAT programme PhD studentship to AG]. | en |
dc.description.abstract | DFT calculations on the full catalytic cycle for manganese catalysed enantioselective hydrogenation of a selection of ketones have been carried out at the PBE0-D3PCM//RI-BP86PCM level. Mn complexes of an enantiomerically pure chiral P,N,N ligand have been found to be most reactive when adopting a facial coordination mode. The use of a new ligand with an ortho-substituted dimethylamino-pyridine motif has been calculated to completely transform the levels of enantioselectivity possible for the hydrogenation of cyclic ketones relative to the first-generation Mn catalysts. In silico evaluation of substrates has been used to identify those likely to be reduced with high enantiomer ratios (er), and others that would exhibit less selectivity; good agreements were then found in experiments. Various cyclic ketones and some acetophenone derivatives were hydrogenated with er's up to 99:1. | |
dc.format.extent | 7 | |
dc.format.extent | 2181941 | |
dc.language.iso | eng | |
dc.relation.ispartof | Angewandte Chemie International Edition | en |
dc.subject | Asymmetric reduction | en |
dc.subject | Computational design | en |
dc.subject | Earth abundant metals | en |
dc.subject | Chirality | en |
dc.subject | Pincer ligands | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject | MCC | en |
dc.subject.lcc | QD | en |
dc.title | Rational design of a facially coordinating P,N,N ligand for manganese-catalysed enantioselective hydrogenation of cyclic ketones | en |
dc.type | Journal article | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.sponsor | IBioIC | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | 10.1002/anie.202212479 | |
dc.description.status | Peer reviewed | en |
dc.identifier.grantnumber | EP/L016419/1 | en |
dc.identifier.grantnumber | en |
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