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CO-free enantioselective hydroformylation of functionalised alkenes : using a dual catalyst system to give improved selectivity and yield

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Pittaway_2019_ASC_CO_free_AAM.pdf (1.539Mb)
Date
13/08/2019
Author
Pittaway, Rachael
Dingwall, Paul
Fuentes, José
Clarke, Matt
Funder
EPSRC
Grant ID
EP/M003868/1
Keywords
Regioselectivity
Hydroformylation
Carbon monoxide surrogates
Asymmetric synthesis
Rhodium
QD Chemistry
DAS
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Abstract
The scope of carbon monoxide-free Asymmetric Transfer HydroFormylation (ATHF) procedures using a highly active single catalyst system derived from 1,2-bis-((2,5)-diphenylphospholano)ethane as chiral ligand has been studied. This reveals some highly successful reactions, but also significant limitations. The development of a new protocol in which a catalyst for formaldehyde decomposition to CO and H2 is combined with the catalyst of choice for the subsequent asymmetric hydroformylation is described. This enables ATHF reactions that were problematic to be significantly improved. The new method has been used in the synthesis of several key precursors to biologically active molecules.
Citation
Pittaway , R , Dingwall , P , Fuentes , J & Clarke , M 2019 , ' CO-free enantioselective hydroformylation of functionalised alkenes : using a dual catalyst system to give improved selectivity and yield ' , Advanced Synthesis & Catalysis , vol. Early View . https://doi.org/10.1002/adsc.201900640
Publication
Advanced Synthesis & Catalysis
Status
Peer reviewed
DOI
https://doi.org/10.1002/adsc.201900640
ISSN
1615-4150
Type
Journal article
Rights
Copyright © 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1002/adsc.201900640
Description
The EPSRC doctoral training grant supported RP (DTG grant: 1518070)). The EPSRC (EP/M003868/1) is also acknowledged for funding (JAF&PD).
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  • University of St Andrews Research
URI
http://hdl.handle.net/10023/20456

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