Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives |
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Authors: | Shuyue Zhang,Mark D. Greenhalgh,Alexandra M. Z. Slawin,Andrew D. Smith |
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Affiliation: | EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews KY16 9ST UK, |
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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.The isothiourea-catalysed enantioselective synthesis of tetrahydroindolizine derivatives containing three stereocentres is reported through a one-pot tandem sequential process. |
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