Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives

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

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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.
Original languageEnglish
Number of pages8
JournalChemical Science
VolumeAdvance Article
Early online date12 Mar 2020
DOIs
Publication statusE-pub ahead of print - 12 Mar 2020

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