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Enantioselective NHC-catalyzed redox [4+2]-hetero-Diels-Alder reactions using α,β-unsaturated trichloromethyl ketones as amide equivalents

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Date
02/10/2015
Author
Attaba, Nassilia
Taylor, James Edward
Slawin, Alexandra Martha Zoya
Smith, Andrew David
Keywords
QD Chemistry
DAS
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Abstract
α,β-Unsaturated trichloromethyl ketones are suitable α,β-unsaturated amide and ester equivalents in N-heterocyclic carbene (NHC)-catalyzed redox hetero-Diels-Alder reactions with azolium enolates generated from α-aroyloxyaldehydes. The initially formed syn-dihydropyranone products can be isolated, or can undergo ring-opening with benzylamine followed by aminolysis of the resulting CCl3 ketone to form a range of diamides with high diastereo- and enantioselectivity (up to >95:5 dr and >99% ee).
Citation
Attaba , N , Taylor , J E , Slawin , A M Z & Smith , A D 2015 , ' Enantioselective NHC-catalyzed redox [4+2]-hetero-Diels-Alder reactions using α,β-unsaturated trichloromethyl ketones as amide equivalents ' , The Journal of Organic Chemistry , vol. 80 , no. 19 , pp. 9728–9739 . https://doi.org/10.1021/acs.joc.5b01820
Publication
The Journal of Organic Chemistry
Status
Peer reviewed
DOI
https://doi.org/10.1021/acs.joc.5b01820
ISSN
0022-3263
Type
Journal article
Rights
Copyright © 2015 American Chemical Society. This work is 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://dx.doi.org/10.1021/acs.joc.5b01820
Description
The authors thank the Royal Society for a University Research Fellowship (A.D.S.) and the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850 (N.A. and J.E.T.).
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  • University of St Andrews Research
URL
http://pubsdc3.acs.org/doi/suppl/10.1021/acs.joc.5b01820
URI
http://hdl.handle.net/10023/9430

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