Issue 15, 2020

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.

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

Supplementary files

Article information

Article type
Edge Article
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
Creative Commons BY license

Chem. Sci., 2020,11, 3885-3892

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, 11, 3885 DOI: 10.1039/D0SC00432D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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