NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides

Davies, Alyn; Greenhalgh, Mark D.; Slawin, Alexandra M. Z.; Smith, Andrew David

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dc.contributor.author	Davies, Alyn
dc.contributor.author	Greenhalgh, Mark D.
dc.contributor.author	Slawin, Alexandra M. Z.
dc.contributor.author	Smith, Andrew David
dc.date.accessioned	2020-07-02T11:30:02Z
dc.date.available	2020-07-02T11:30:02Z
dc.date.issued	2020-06-30
dc.identifier.citation	Davies , A , Greenhalgh , M D , Slawin , A M Z & Smith , A D 2020 , ' NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides ' , Beilstein Journal of Organic Chemistry , vol. 16 , pp. 1572-1578 . https://doi.org/10.3762/bjoc.16.129	en
dc.identifier.issn	1860-5397
dc.identifier.other	PURE: 268315110
dc.identifier.other	PURE UUID: 1db15215-bfa6-46e1-a288-b94927f964b7
dc.identifier.other	ORCID: /0000-0002-2104-7313/work/76775887
dc.identifier.other	ORCID: /0000-0002-9527-6418/work/76776803
dc.identifier.other	WOS: 000548546100002
dc.identifier.other	Scopus: 85090573144
dc.identifier.uri	https://hdl.handle.net/10023/20193
dc.description	Authors acknowlege the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC grant agreement no. 279850 (A.T.D.). We also thank the EPSRC UK National Mass Spectrometry Facility at Swansea University.	en
dc.description.abstract	The N-heterocyclic carbene (NHC) catalyzed formal [2+2] cycloaddition between α-aroyloxyaldehydes and trifluoroacetophenones, followed by ring-opening with an amine or reducing agent is described. The resulting β-hydroxy-β-trifluoromethyl amide and alcohol products are produced with reasonable diastereocontrol (typically ~70:30 dr) and excellent enantioselectivity, and can be isolated in moderate to good yield as a single diastereoisomer.
dc.language.iso	eng
dc.relation.ispartof	Beilstein Journal of Organic Chemistry	en
dc.rights	Copyright © 2020 Davies et al.; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited.	en
dc.subject	Trifluoromethyl group	en
dc.subject	N-heterocyclic carbene	en
dc.subject	Enantioselective catalysis	en
dc.subject	Formal [2+2]-cycloaddition	en
dc.subject	Ring-opening	en
dc.subject	QD Chemistry	en
dc.subject	DAS	en
dc.subject.lcc	QD	en
dc.title	NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides	en
dc.type	Journal article	en
dc.contributor.sponsor	European Commission	en
dc.description.version	Publisher PDF	en
dc.contributor.institution	University of St Andrews. School of Chemistry	en
dc.contributor.institution	University of St Andrews. EaSTCHEM	en
dc.identifier.doi	https://doi.org/10.3762/bjoc.16.129
dc.description.status	Peer reviewed	en
dc.identifier.grantnumber	N/A	en

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