Exploring the scope of the isothiourea-mediated synthesis of dihydropyridinones

Pei Pei Yeh; David S.B. Daniels; Charlene Fallan; Eoin Gould; Carmen Simal; James E. Taylor; Alexandra M.Z. Slawin; Andrew D. Smith

doi:10.1039/c4ob02408g

Exploring the scope of the isothiourea-mediated synthesis of dihydropyridinones

Pei Pei Yeh, David S.B. Daniels, Charlene Fallan, Eoin Gould, Carmen Simal, James E. Taylor, Alexandra M.Z. Slawin, Andrew D. Smith

Department of Chemistry

University of St Andrews

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

38 Citations (SciVal)

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. This journal is

Original language	English
Pages (from-to)	2177-2191
Number of pages	15
Journal	Organic and 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

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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AU - Daniels, David S.B.

AU - Fallan, Charlene

AU - Gould, Eoin

AU - Simal, Carmen

AU - Taylor, James E.

AU - Slawin, Alexandra M.Z.

AU - Smith, Andrew D.

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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. This journal is

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JF - Organic and Biomolecular Chemistry

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ER -

Exploring the scope of the isothiourea-mediated synthesis of dihydropyridinones

Abstract

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