Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives

Shuyue Zhang; Mark David Greenhalgh; Alexandra Martha Zoya Slawin; Andrew David Smith

doi:10.1039/D0SC00432D

Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives

Shuyue Zhang, Mark David Greenhalgh, Alexandra Martha Zoya Slawin, Andrew David Smith

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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.

Original language	English
Number of pages	8
Journal	Chemical Science
Volume	Advance Article
Early online date	12 Mar 2020
DOIs	https://doi.org/10.1039/D0SC00432D
Publication status	E-pub ahead of print - 12 Mar 2020

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10.1039/D0SC00432DLicence: CC BY

Zhang_2020_CS_Tandem_CC
Copyright © 2020 The Author(s). Open Access Article. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Final published version, 2 MBLicence: CC BY

RS Wolfson Merit Award: Developing Catalysis Research: New Reaction Discoveries and Practical Applications
Smith, A. D. (PI)
The Royal Society
1/01/15 → 31/12/19
Project: Fellowship
ERC Starting Grant EnolCat: Emulating nature: Reaction diversity and understanding through asymmetric catalysis
Smith, A. D. (PI)
European Commission
1/10/11 → 30/06/17
Project: Standard

Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives (dataset)
Smith, A. D. (Creator), Greenhalgh, M. D. (Owner), Slawin, A. M. Z. (Creator) & Zhang, S. (Creator), University of St Andrews, 20 Jan 2020
DOI: 10.17630/7bc9507c-e817-4da7-988a-02fcd1a6f4fa
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title = "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.",

author = "Shuyue Zhang and Greenhalgh, {Mark David} and Slawin, {Alexandra Martha Zoya} and Smith, {Andrew David}",

note = "The research leading to these results (S.Z.) has received funding from the ERC under the European Union{\textquoteright}s Seventh Framework Programme (FP7/2007–2013)/ERC grant agreement no 279850. A.D.S. thanks the Royal Society for a Wolfson Research Merit Award.",

year = "2020",

month = mar,

day = "12",

doi = "10.1039/D0SC00432D",

language = "English",

volume = "Advance Article",

journal = "Chemical Science",

issn = "2041-6520",

publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives

AU - Zhang, Shuyue

AU - Greenhalgh, Mark David

AU - Slawin, Alexandra Martha Zoya

AU - Smith, Andrew David

N1 - The research leading to these results (S.Z.) has received funding from the ERC under the European Union’s Seventh Framework Programme (FP7/2007–2013)/ERC grant agreement no 279850. A.D.S. thanks the Royal Society for a Wolfson Research Merit Award.

PY - 2020/3/12

Y1 - 2020/3/12

N2 - 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.

AB - 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.

U2 - 10.1039/D0SC00432D

DO - 10.1039/D0SC00432D

M3 - Article

SN - 2041-6520

VL - Advance Article

JO - Chemical Science

JF - Chemical Science

ER -

Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives

Abstract

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Projects

RS Wolfson Merit Award: Developing Catalysis Research: New Reaction Discoveries and Practical Applications

ERC Starting Grant EnolCat: Emulating nature: Reaction diversity and understanding through asymmetric catalysis

Datasets

Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives (dataset)

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