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Phospholane-phosphite ligands for Rh catalyzed enantioselective conjugate addition : unusually reactive catalysts for challenging couplings

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Gilbert_2020_EJOC_Rh_CC.pdf (1007.Kb)
Date
25/05/2020
Author
Gilbert, Sophie H.
Fuentes, José A.
Cordes, David B.
Slawin, Alexandra M. Z.
Clarke, Matthew L.
Keywords
Asymmetric arylation
Michael addition
Aryl boronic acids
Phospholane ligands
Asymmetric catalysis
QD Chemistry
DAS
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Abstract
The use of Rh catalysts derived from a phospholane-phosphite ligand were found to be more productive than the classic rhodium/BINAP system in enantioselective conjugate additions. These catalysts enable the use of lower amounts of aryl boronic acid in an asymmetric arylation reaction that required an impractical excess of nucleophile. This catalyst was also found to enable the coupling of a poorly reactive Michael acceptor, N-CBz-2-3-dehydro-4-piperidone, or the coupling of poorly reactive 2-furyl boronic acids at ambient or near temperatures.
Citation
Gilbert , S H , Fuentes , J A , Cordes , D B , Slawin , A M Z & Clarke , M L 2020 , ' Phospholane-phosphite ligands for Rh catalyzed enantioselective conjugate addition : unusually reactive catalysts for challenging couplings ' , European Journal of Organic Chemistry , vol. 2020 , no. 20 , pp. 3071-3076 . https://doi.org/10.1002/ejoc.202000336
Publication
European Journal of Organic Chemistry
Status
Peer reviewed
DOI
https://doi.org/10.1002/ejoc.202000336
ISSN
1434-193X
Type
Journal article
Rights
Copyright © 2020 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Description
We would like to thank the University of St Andrews, and the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT) for financial support [Ph.D. studentship to SG; Grant code: EP/L016419/1], and the EPSRC for funding of JAF (EP/M003868/1).
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  • University of St Andrews Research
URI
http://hdl.handle.net/10023/20126

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