Enantioselective isothiourea-catalysed trans-dihydropyridinone synthesis using saccharin-derived ketimines : scope and limitations

Stark, Daniel Graham; Young, Claire Mary; O'Riordan, Timothy J C; Slawin, Alexandra Martha Zoya; Smith, Andrew David

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dc.contributor.author	Stark, Daniel Graham
dc.contributor.author	Young, Claire Mary
dc.contributor.author	O'Riordan, Timothy J C
dc.contributor.author	Slawin, Alexandra Martha Zoya
dc.contributor.author	Smith, Andrew David
dc.date.accessioned	2016-08-19T09:40:10Z
dc.date.available	2016-08-19T09:40:10Z
dc.date.issued	2016-09-14
dc.identifier.citation	Stark , D G , Young , C M , O'Riordan , T J C , Slawin , A M Z & Smith , A D 2016 , ' Enantioselective isothiourea-catalysed trans -dihydropyridinone synthesis using saccharin-derived ketimines : scope and limitations ' , Organic & Biomolecular Chemistry , vol. 14 , no. 34 , pp. 8068-8073 . https://doi.org/10.1039/C6OB01473A	en
dc.identifier.issn	1477-0520
dc.identifier.other	PURE: 244566038
dc.identifier.other	PURE UUID: aa8bd179-6ffe-44f5-a791-a64dc27659d9
dc.identifier.other	Scopus: 84984656800
dc.identifier.other	ORCID: /0000-0002-2104-7313/work/36567487
dc.identifier.other	ORCID: /0000-0002-9527-6418/work/56861938
dc.identifier.other	WOS: 000382058000012
dc.identifier.uri	http://hdl.handle.net/10023/9332
dc.description	The authors thank Syngenta and the EPSRC (grant code EP/K503162/1) (DGS) for funding. The European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850 is also acknowledged (CMY). ADS thanks the Royal Society for a Wolfson Research Merit Award. We also thank the EPSRC UK National Mass Spectrometry Facility at Swansea University.	en
dc.description.abstract	The catalytic enantioselective synthesis of a range of trans-dihydropyridinones from aryl-, heteroaryl- and alkenylacetic acids and saccharin-derived ketimines with good to excellent stereocontrol (15 examples, up to >95:5 dr, up to >99:1 er) is reported. After extensive optimisation, HyperBTM proved the optimal isothiourea catalyst for this transformation at −78 °C, giving trans-dihydropyridones with generally excellent levels of diastereo- and enantioselectivity.
dc.format.extent	6
dc.language.iso	eng
dc.relation.ispartof	Organic & Biomolecular Chemistry	en
dc.rights	Copyright 2016 the Authors. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.	en
dc.subject	QD Chemistry	en
dc.subject	DAS	en
dc.subject.lcc	QD	en
dc.title	Enantioselective isothiourea-catalysed trans-dihydropyridinone synthesis using saccharin-derived ketimines : scope and limitations	en
dc.type	Journal article	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.Biomedical Sciences Research Complex	en
dc.contributor.institution	University of St Andrews.EaSTCHEM	en
dc.identifier.doi	https://doi.org/10.1039/C6OB01473A
dc.description.status	Peer reviewed	en
dc.identifier.url	http://www.rsc.org/suppdata/c6/ob/c6ob01473a/c6ob01473a1.pdf	en

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