Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives

Zhang, Shuyue; Greenhalgh, Mark David; Slawin, Alexandra Martha Zoya; Smith, Andrew David

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dc.contributor.author	Zhang, Shuyue
dc.contributor.author	Greenhalgh, Mark David
dc.contributor.author	Slawin, Alexandra Martha Zoya
dc.contributor.author	Smith, Andrew David
dc.date.accessioned	2020-03-26T17:30:03Z
dc.date.available	2020-03-26T17:30:03Z
dc.date.issued	2020-03-12
dc.identifier.citation	Zhang , S , Greenhalgh , M D , Slawin , A M Z & Smith , A D 2020 , ' Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives ' , Chemical Science , vol. Advance Article . https://doi.org/10.1039/D0SC00432D	en
dc.identifier.issn	2041-6520
dc.identifier.other	PURE: 266762426
dc.identifier.other	PURE UUID: d3a3015a-76b3-4c75-9886-95d02d24169c
dc.identifier.other	ORCID: /0000-0002-2104-7313/work/70618872
dc.identifier.other	ORCID: /0000-0002-9527-6418/work/70618948
dc.identifier.other	WOS: 000527022500012
dc.identifier.other	Scopus: 85083682459
dc.identifier.uri	https://hdl.handle.net/10023/19715
dc.description	The research leading to these results (S.Z.) has received funding from the ERC under the European Union’s Seventh Framework Programme (FP7/2007–2013)/ERC grant agreement no 279850. A.D.S. thanks the Royal Society for a Wolfson Research Merit Award.	en
dc.description.abstract	An isothiourea-catalysed enantioselective synthesis of novel tetrahydroindolizine derivatives is reported through a one-pot tandem sequential process. The application of 2-(pyrrol-1-yl)acetic acid in combination with either a trifluoromethyl enone or an α-keto-β,γ-unsaturated ester in an enantioselective Michael addition-lactonisation process, followed by in situ ring-opening and cyclisation, led to a range of 24 tetrahydroindolizine derivatives containing three stereocentres in up to > 95:5 dr and > 99:1 er.
dc.format.extent	8
dc.language.iso	eng
dc.relation.ispartof	Chemical Science	en
dc.rights	Copyright © 2020 The Author(s). Open Access Article. 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	Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives	en
dc.type	Journal article	en
dc.contributor.sponsor	European Commission	en
dc.contributor.sponsor	The Royal Society	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. EaSTCHEM	en
dc.identifier.doi	https://doi.org/10.1039/D0SC00432D
dc.description.status	Peer reviewed	en
dc.identifier.grantnumber	N/A	en
dc.identifier.grantnumber	WM140071	en

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