Enantioselective isothiourea-catalysed trans-dihydropyridinone synthesis using saccharin-derived ketimines: scope and limitations

Daniel Graham Stark; Claire Mary Young; Timothy J C O'Riordan; Alexandra Martha Zoya Slawin; Andrew David Smith

doi:10.1039/C6OB01473A

Enantioselective isothiourea-catalysed trans-dihydropyridinone synthesis using saccharin-derived ketimines: scope and limitations

Daniel Graham Stark, Claire Mary Young, Timothy J C O'Riordan, Alexandra Martha Zoya Slawin, Andrew David Smith

Research output: Contribution to journal › Article › peer-review

Abstract

The catalytic enantioselective synthesis of a range of trans-dihydropyridinones from aryl-, heteroaryl- and alkenylacetic acids and saccharin-derived ketimines with good to excellent stereocontrol (15 examples, up to >95:5 dr, up to >99:1 er) is reported. After extensive optimisation, HyperBTM proved the optimal isothiourea catalyst for this transformation at −78 °C, giving trans-dihydropyridones with generally excellent levels of diastereo- and enantioselectivity.

Original language	English
Pages (from-to)	8068-8073
Number of pages	6
Journal	Organic & Biomolecular Chemistry
Volume	14
Issue number	34
Early online date	26 Jul 2016
DOIs	https://doi.org/10.1039/C6OB01473A
Publication status	Published - 14 Sept 2016

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10.1039/C6OB01473ALicence: CC BY

Stark_2016_OBCc6ob01473a_CCBY
Copyright 2016 the Authors. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Final published version, 2.05 MBLicence: CC BY

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title = "Enantioselective isothiourea-catalysed trans-dihydropyridinone synthesis using saccharin-derived ketimines: scope and limitations",

abstract = "The catalytic enantioselective synthesis of a range of trans-dihydropyridinones from aryl-, heteroaryl- and alkenylacetic acids and saccharin-derived ketimines with good to excellent stereocontrol (15 examples, up to >95:5 dr, up to >99:1 er) is reported. After extensive optimisation, HyperBTM proved the optimal isothiourea catalyst for this transformation at −78 °C, giving trans-dihydropyridones with generally excellent levels of diastereo- and enantioselectivity. ",

author = "Stark, {Daniel Graham} and Young, {Claire Mary} and O'Riordan, {Timothy J C} and Slawin, {Alexandra Martha Zoya} and Smith, {Andrew David}",

note = "The authors thank Syngenta and the EPSRC (grant code EP/K503162/1) (DGS) for funding. The European Research Council under the European Union{\textquoteright}s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850 is also acknowledged (CMY). ADS thanks the Royal Society for a Wolfson Research Merit Award. We also thank the EPSRC UK National Mass Spectrometry Facility at Swansea University.",

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doi = "10.1039/C6OB01473A",

language = "English",

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journal = "Organic & Biomolecular Chemistry",

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T1 - Enantioselective isothiourea-catalysed trans-dihydropyridinone synthesis using saccharin-derived ketimines

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AU - Stark, Daniel Graham

AU - Young, Claire Mary

AU - O'Riordan, Timothy J C

AU - Slawin, Alexandra Martha Zoya

AU - Smith, Andrew David

N1 - The authors thank Syngenta and the EPSRC (grant code EP/K503162/1) (DGS) for funding. The European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850 is also acknowledged (CMY). ADS thanks the Royal Society for a Wolfson Research Merit Award. We also thank the EPSRC UK National Mass Spectrometry Facility at Swansea University.

PY - 2016/9/14

Y1 - 2016/9/14

N2 - The catalytic enantioselective synthesis of a range of trans-dihydropyridinones from aryl-, heteroaryl- and alkenylacetic acids and saccharin-derived ketimines with good to excellent stereocontrol (15 examples, up to >95:5 dr, up to >99:1 er) is reported. After extensive optimisation, HyperBTM proved the optimal isothiourea catalyst for this transformation at −78 °C, giving trans-dihydropyridones with generally excellent levels of diastereo- and enantioselectivity.

AB - The catalytic enantioselective synthesis of a range of trans-dihydropyridinones from aryl-, heteroaryl- and alkenylacetic acids and saccharin-derived ketimines with good to excellent stereocontrol (15 examples, up to >95:5 dr, up to >99:1 er) is reported. After extensive optimisation, HyperBTM proved the optimal isothiourea catalyst for this transformation at −78 °C, giving trans-dihydropyridones with generally excellent levels of diastereo- and enantioselectivity.

UR - http://www.rsc.org/suppdata/c6/ob/c6ob01473a/c6ob01473a1.pdf

U2 - 10.1039/C6OB01473A

DO - 10.1039/C6OB01473A

M3 - Article

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JF - Organic & Biomolecular Chemistry

IS - 34

ER -

Enantioselective isothiourea-catalysed trans-dihydropyridinone synthesis using saccharin-derived ketimines: scope and limitations

Abstract

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

Data underpinning - Enantioselective Isothiourea-Catalysed trans-Dihydropyridinone Synthesis using Saccharin-derived Ketimines: Scope and Limitations

Cite this

Enantioselective isothiourea-catalysed trans-dihydropyridinone synthesis using saccharin-derived ketimines: scope and limitations

Abstract

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Projects

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

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Data underpinning - Enantioselective Isothiourea-Catalysed trans-Dihydropyridinone Synthesis using Saccharin-derived Ketimines: Scope and Limitations

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