Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives
Shuyue Zhang1, Mark D Greenhalgh1, Alexandra M Z Slawin1
1EaStCHEM, School of Chemistry, University of St Andrews North Haugh St Andrews KY16 9ST UK ads10@st-andrews.ac.uk.
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.
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