Tandem Sequential Catalytic Enantioselective Synthesis of Highly-functionalised Tetrahydroindolizine Derivatives

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2021 Jun 14

PMID 34122857

Citations 9

Authors

Shuyue Zhang

Mark D Greenhalgh

Alexandra M Z Slawin

Andrew D Smith

Affiliations

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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 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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