Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives
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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.
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
Copyright © 2020 The Author(s). Open Access Article. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
DescriptionThe 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.
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