Exploring the scope of the isothiourea-mediated synthesis of dihydropyridinones

Pei-Pei Yeh; David Sydney Bernard Daniels; Charlene Fallan; Eoin Rory Gould; Carmen Simal Fernandez; James Edward Taylor; Alexandra Martha Zoya Slawin; Andrew David Smith

doi:10.1039/c4ob02408g

Exploring the scope of the isothiourea-mediated synthesis of dihydropyridinones

Pei-Pei Yeh
, David Sydney Bernard Daniels
, Charlene Fallan
, Eoin Rory Gould
, Carmen Simal Fernandez
, James Edward Taylor
, Alexandra Martha Zoya Slawin
, Andrew David Smith

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

Abstract

The exploration and expansion of the scope of the isothiourea-mediated synthesis of dihydropyridinones is presented. The use of ketimines derived from α,β-unsaturated γ-ketoesters as the Michael acceptor in a Michael addition / lactamisation cascade gives access to a range of dihydropyridinones with high enantioselectivity. The nature of the N-sulfonyl group present on the ketimine is extensively investigated, with further studies into derivatisation of the dihydropyridinone core also reported.

Original language	English
Pages (from-to)	2177-2191
Journal	Organic & Biomolecular Chemistry
Volume	13
Issue number	7
Early online date	2 Jan 2015
DOIs	https://doi.org/10.1039/c4ob02408g
Publication status	Published - 21 Feb 2015

Keywords

Derivatisation
High enantioselectivity
Isothiourea
Ketimines
Keto ester
Michael acceptors
Michael additions
Sulfonyl groups

Access to Document

10.1039/c4ob02408g

Dihydropyridinones
© 2014, the Authors. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at http://doi.org/10.1039/C4OB02408G
Accepted author manuscript, 518 KB

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Structuring the Future: Structuring the Future - Underpinning world-leading science in EaStCHEM through cutting edge characterisation
Woollins, J. D. (PI), Ashbrook, S. E. (CoI), Morris, R. (CoI) & Slawin, A. (CoI)
EPSRC
1/01/13 → 31/03/13
Project: Standard
Clean catalysis for sustainable develop: Clean catalysis for sustainable development
Smith, A. (PI)
EPSRC
1/11/12 → 31/10/17
Project: Standard
Clean catalysis for sustainable develop: Clean catalysis for sustainable development
Kamer, P. C. J. (PI)
EPSRC
1/11/12 → 31/10/17
Project: Standard

Exploring the scope of the isothiourea-mediated synthesis of dihydropyridinones (dataset)
Yeh, P.-P. (Creator), Daniels, D. S. B. (Creator), Fallan, C. (Creator), Gould, E. R. (Creator), Simal Fernandez, C. (Creator), Taylor, J. E. (Creator), Slawin, A. M. Z. (Creator) & Smith, A. D. (Creator), Cambridge Crystallographic Data Centre, 2014
https://dx.doi.org/10.5517/cc13pz5y and one more link, https://dx.doi.org/10.5517/cc13pz6z (show fewer)
Dataset

Cite this

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title = "Exploring the scope of the isothiourea-mediated synthesis of dihydropyridinones",

abstract = "The exploration and expansion of the scope of the isothiourea-mediated synthesis of dihydropyridinones is presented. The use of ketimines derived from α,β-unsaturated γ-ketoesters as the Michael acceptor in a Michael addition / lactamisation cascade gives access to a range of dihydropyridinones with high enantioselectivity. The nature of the N-sulfonyl group present on the ketimine is extensively investigated, with further studies into derivatisation of the dihydropyridinone core also reported.",

keywords = "Derivatisation, High enantioselectivity, Isothiourea, Ketimines, Keto ester, Michael acceptors, Michael additions, Sulfonyl groups",

author = "Pei-Pei Yeh and Daniels, \{David Sydney Bernard\} and Charlene Fallan and Gould, \{Eoin Rory\} and \{Simal Fernandez\}, Carmen and Taylor, \{James Edward\} and Slawin, \{Alexandra Martha Zoya\} and Smith, \{Andrew David\}",

note = "The authors thank the Royal Society for a University Research Fellowship (ADS), the EU (IEF for CS) and the European Research Council under the European Union{\textquoteright}s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850 (JET and CF) and the EPSRC grant numbers EP/J018139/1 (DSBD) and EP/K00445X/1 (EG) for funding. ",

year = "2015",

month = feb,

day = "21",

doi = "10.1039/c4ob02408g",

language = "English",

volume = "13",

pages = "2177--2191",

journal = "Organic \& Biomolecular Chemistry",

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AU - Yeh, Pei-Pei

AU - Daniels, David Sydney Bernard

AU - Fallan, Charlene

AU - Gould, Eoin Rory

AU - Simal Fernandez, Carmen

AU - Taylor, James Edward

AU - Slawin, Alexandra Martha Zoya

AU - Smith, Andrew David

N1 - The authors thank the Royal Society for a University Research Fellowship (ADS), the EU (IEF for CS) and the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850 (JET and CF) and the EPSRC grant numbers EP/J018139/1 (DSBD) and EP/K00445X/1 (EG) for funding.

PY - 2015/2/21

Y1 - 2015/2/21

N2 - The exploration and expansion of the scope of the isothiourea-mediated synthesis of dihydropyridinones is presented. The use of ketimines derived from α,β-unsaturated γ-ketoesters as the Michael acceptor in a Michael addition / lactamisation cascade gives access to a range of dihydropyridinones with high enantioselectivity. The nature of the N-sulfonyl group present on the ketimine is extensively investigated, with further studies into derivatisation of the dihydropyridinone core also reported.

AB - The exploration and expansion of the scope of the isothiourea-mediated synthesis of dihydropyridinones is presented. The use of ketimines derived from α,β-unsaturated γ-ketoesters as the Michael acceptor in a Michael addition / lactamisation cascade gives access to a range of dihydropyridinones with high enantioselectivity. The nature of the N-sulfonyl group present on the ketimine is extensively investigated, with further studies into derivatisation of the dihydropyridinone core also reported.

KW - Derivatisation

KW - High enantioselectivity

KW - Isothiourea

KW - Ketimines

KW - Keto ester

KW - Michael acceptors

KW - Michael additions

KW - Sulfonyl groups

U2 - 10.1039/c4ob02408g

DO - 10.1039/c4ob02408g

M3 - Article

C2 - 25553730

SN - 1477-0520

VL - 13

SP - 2177

EP - 2191

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 7

ER -

Exploring the scope of the isothiourea-mediated synthesis of dihydropyridinones

Abstract

Keywords

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Projects

Structuring the Future: Structuring the Future - Underpinning world-leading science in EaStCHEM through cutting edge characterisation

Clean catalysis for sustainable develop: Clean catalysis for sustainable development

Clean catalysis for sustainable develop: Clean catalysis for sustainable development

Datasets

Exploring the scope of the isothiourea-mediated synthesis of dihydropyridinones (dataset)

Cite this