Enantioselective stereodivergent nucleophile-dependent isothiourea-catalysed domino reactions
Date
05/12/2016Author
Grant ID
EP/J018139/1
WM140071
EP/J018139/1
Keywords
Metadata
Show full item recordAbstract
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
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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