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Bew, Sean P. 
ORCID: https://orcid.org/0000-0002-9087-9463, Stephenson, G. Richard ORCID: https://orcid.org/0000-0003-1487-9178, Rouden, Jacques, Ashford, Polly Anna, Bourane, Manuel, Charvet, Agathe, Dalstein, Virginie M D, Jauseau, Raphael, Hiatt-Gipson, G. D. and Martinez-Lozano, Luis A.
(2015)
Bioinspired, base- and metal-free, mild decarboxylative aldol activation of malonic acid half thioesters under phase-transfer reaction conditions.
Advanced Synthesis & Catalysis, 357 (6).
pp. 1245-1257.
ISSN 1615-4150
Abstract
Utilizing ‘off the shelf’ commercially available, cheap, small synthetic molecules that mimic the efficient mediation of important bioreactions utilized by Nature is not only highly sought after but also currently highly topical. This paper details our preliminary efforts at developing a unique base- and metal-free phase-transfer-mediated malonic acid thioester (MAHT) ‘activation protocol’ that efficiently generates (±)-β-thioesters. Our bioinspired aldol process is exceptionally mild, conducted under near neutral pH reaction conditions, does not require an inert, oxygen-free atmosphere or anhydrous reaction conditions and is highly atom-economic. Exemplifying the utility of our protocol, the synthesis of an array of structurally and functionally diverse (±)-β-hydroxy thioesters equipped with highly prized functionality, i.e., chlorine, bromine, fluorine, nitrile and nitro groups, is reported, as is the diastereoselective potential of this important reaction.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | aldol reaction,base-free conditions,decarboxylation,metal-free conditions,phase-transfer process |
| Faculty \ School: | Faculty of Science > School of Chemistry Faculty of Medicine and Health Sciences > Norwich Medical School Faculty of Science > School of Chemical Sciences and Pharmacy (former - to 2009) Faculty of Science |
| UEA Research Groups: | Faculty of Science > Research Groups > Chemistry of Materials and Catalysis Faculty of Medicine and Health Sciences > Research Groups > Norwich Clinical Trials Unit Faculty of Medicine and Health Sciences > Research Groups > Public Health and Health Services Research (former - to 2023) |
| Related URLs: | |
| Depositing User: | Pure Connector |
| Date Deposited: | 08 Apr 2015 09:00 |
| Last Modified: | 21 Oct 2022 00:48 |
| URI: | https://ueaeprints.uea.ac.uk/id/eprint/53094 |
| DOI: | 10.1002/adsc.201400915 |
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