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Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives.

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.

SUBMITTER: Zhang S

PROVIDER: S-EPMC8152628 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives.

Zhang Shuyue S Greenhalgh Mark D MD Slawin Alexandra M Z AMZ Smith Andrew D AD

Chemical science 20200312 15

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 ...[more]

PMID: 34122857

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