Enantioselective synthesis of 3,5,6-substituted dihydropyranones and dihydropyridinones using isothiourea-mediated catalysis

Daniel Graham Stark; Louis Christian Morrill; David Bradford Cordes; Alexandra Martha Zoya Slawin; Timothy J.C. O'Riordan; Andrew David Smith

doi:10.1002/asia.201500907

Enantioselective synthesis of 3,5,6-substituted dihydropyranones and dihydropyridinones using isothiourea-mediated catalysis

Daniel Graham Stark, Louis Christian Morrill, David Bradford Cordes, Alexandra Martha Zoya Slawin, Timothy J.C. O'Riordan, Andrew David Smith

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Abstract

The scope of dihydropyranone and dihydropyridinone products accessible by isothiourea-catalysed processes has been expanded and explored through the use of 2-N-tosyliminoacrylates and 2-aroylacrylates in a Michael addition-lactonisation/lactamisation cascade. Notably, in order to ensure reproducibility it is essential to use homoanhydrides as ammonium enolate precursors with 2-aroyl acrylates, while carboxylic acids can be used with 2-N-tosyliminoacrylates, delivering a range of 3,5,6-substituted dihydropyranones and dihydropyridinones with high enantioselectivity (typically >90% ee). The derivatisation of the heterocyclic core of a model 3,5,6-substituted dihydropyranone through hydrogenation is also reported.

Original language	English
Pages (from-to)	395–400
Number of pages	7
Journal	Chemistry-An Asian Journal
Volume	11
Issue number	3
Early online date	12 Nov 2015
DOIs	https://doi.org/10.1002/asia.201500907
Publication status	Published - 4 Feb 2016

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Smith_et_al-2015-Chemistry-An_Asian_Journal_CC
Copyright 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
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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

Data underpinning "Enantioselective Synthesis of 3,5,6-Substituted Dihydropyranones and Dihydropyridinones using Isothiourea-Mediated Catalysis"
Stark, D. G. (Creator), Morrill, L. C. (Creator), Cordes, D. B. (Creator), Slawin, A. M. Z. (Creator), O'Riordan, T. (Creator) & Smith, A. D. (Creator), University of St Andrews, 2015
DOI: 10.17630/6E0AD60A-DDF5-459C-BC45-CDD80FD518B8
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title = "Enantioselective synthesis of 3,5,6-substituted dihydropyranones and dihydropyridinones using isothiourea-mediated catalysis",

abstract = "The scope of dihydropyranone and dihydropyridinone products accessible by isothiourea-catalysed processes has been expanded and explored through the use of 2-N-tosyliminoacrylates and 2-aroylacrylates in a Michael addition-lactonisation/lactamisation cascade. Notably, in order to ensure reproducibility it is essential to use homoanhydrides as ammonium enolate precursors with 2-aroyl acrylates, while carboxylic acids can be used with 2-N-tosyliminoacrylates, delivering a range of 3,5,6-substituted dihydropyranones and dihydropyridinones with high enantioselectivity (typically >90% ee). The derivatisation of the heterocyclic core of a model 3,5,6-substituted dihydropyranone through hydrogenation is also reported.",

author = "Stark, {Daniel Graham} and Morrill, {Louis Christian} and Cordes, {David Bradford} and Slawin, {Alexandra Martha Zoya} and O'Riordan, {Timothy J.C.} and Smith, {Andrew David}",

note = "We thank the Royal Society for a University Research Fellowship (ADS), Syngenta and EPSRC grant No. EP/K503162/1 (DGS), and the European Research Council under the European Union{\textquoteright}s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850, for funding. ",

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doi = "10.1002/asia.201500907",

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volume = "11",

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T1 - Enantioselective synthesis of 3,5,6-substituted dihydropyranones and dihydropyridinones using isothiourea-mediated catalysis

AU - Stark, Daniel Graham

AU - Morrill, Louis Christian

AU - Cordes, David Bradford

AU - Slawin, Alexandra Martha Zoya

AU - O'Riordan, Timothy J.C.

AU - Smith, Andrew David

N1 - We thank the Royal Society for a University Research Fellowship (ADS), Syngenta and EPSRC grant No. EP/K503162/1 (DGS), and the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850, for funding.

PY - 2016/2/4

Y1 - 2016/2/4

N2 - The scope of dihydropyranone and dihydropyridinone products accessible by isothiourea-catalysed processes has been expanded and explored through the use of 2-N-tosyliminoacrylates and 2-aroylacrylates in a Michael addition-lactonisation/lactamisation cascade. Notably, in order to ensure reproducibility it is essential to use homoanhydrides as ammonium enolate precursors with 2-aroyl acrylates, while carboxylic acids can be used with 2-N-tosyliminoacrylates, delivering a range of 3,5,6-substituted dihydropyranones and dihydropyridinones with high enantioselectivity (typically >90% ee). The derivatisation of the heterocyclic core of a model 3,5,6-substituted dihydropyranone through hydrogenation is also reported.

AB - The scope of dihydropyranone and dihydropyridinone products accessible by isothiourea-catalysed processes has been expanded and explored through the use of 2-N-tosyliminoacrylates and 2-aroylacrylates in a Michael addition-lactonisation/lactamisation cascade. Notably, in order to ensure reproducibility it is essential to use homoanhydrides as ammonium enolate precursors with 2-aroyl acrylates, while carboxylic acids can be used with 2-N-tosyliminoacrylates, delivering a range of 3,5,6-substituted dihydropyranones and dihydropyridinones with high enantioselectivity (typically >90% ee). The derivatisation of the heterocyclic core of a model 3,5,6-substituted dihydropyranone through hydrogenation is also reported.

U2 - 10.1002/asia.201500907

DO - 10.1002/asia.201500907

M3 - Article

SN - 1861-4728

VL - 11

SP - 395

EP - 400

JO - Chemistry-An Asian Journal

JF - Chemistry-An Asian Journal

IS - 3

ER -

Enantioselective synthesis of 3,5,6-substituted dihydropyranones and dihydropyridinones using isothiourea-mediated catalysis

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

Datasets

Data underpinning "Enantioselective Synthesis of 3,5,6-Substituted Dihydropyranones and Dihydropyridinones using Isothiourea-Mediated Catalysis"

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