Enantioselective stereodivergent nucleophile-dependent isothiourea-catalysed domino reactions
Date
05/12/2016Author
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Abstract
α,β-Unsaturated acyl ammoniums generated from the reaction of α,β-unsaturated 2,4,6-trichlorophenol (TCP) esters bearing a pendent enone with an isothiourea organocatalyst are versatile intermediates in a range of enantioselective nucleophile-dependent domino processes to form complex products of diverse topology with excellent stereoselectivity. Use of either 1,3-dicarbonyls, acyl benzothiazoles, or acyl benzimidazoles as nucleophiles allows three distinct, diastereodivergent domino reaction pathways to be accessed to form various fused polycyclic cores containing multiple contiguous stereocentres.
Citation
Matviitsuk , A , Taylor , J E , Cordes , D B , Slawin , A M Z & Smith , A D 2016 , ' Enantioselective stereodivergent nucleophile-dependent isothiourea-catalysed domino reactions ' , Chemistry - A European Journal , vol. 22 , no. 49 , pp. 17748-17757 . https://doi.org/10.1002/chem.201603318
Publication
Chemistry - A European Journal
Status
Peer reviewed
ISSN
0947-6539Type
Journal article
Rights
© 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Description
We thank the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007–2013) ERC grant agreement no. 279850 (J.E.T.) and the EPSRC (EP/J018139/1, A.M.). ADS thanks the Royal Society for a Wolfson Research Merit Award.Collections
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