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

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Davies_2020_BJOC_NHC_CC.pdf (856.0Kb)
Date
30/06/2020
Author
Davies, Alyn
Greenhalgh, Mark D.
Slawin, Alexandra M. Z.
Smith, Andrew David
Keywords
Trifluoromethyl group
N-heterocyclic carbene
Enantioselective catalysis
Formal [2+2]-cycloaddition
Ring-opening
QD Chemistry
DAS
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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.
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
Publication
Beilstein Journal of Organic Chemistry
Status
Peer reviewed
DOI
https://doi.org/10.3762/bjoc.16.129
ISSN
1860-5397
Type
Journal article
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.
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.
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  • University of St Andrews Research
URI
http://hdl.handle.net/10023/20193

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