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Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives

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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.

Graphical abstract: Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives

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Article information


Submitted
23 Jan 2020
Accepted
06 Mar 2020
First published
12 Mar 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives

S. Zhang, M. D. Greenhalgh, Alexandra M. Z. Slawin and A. D. Smith, Chem. Sci., 2020, Advance Article , DOI: 10.1039/D0SC00432D

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