Issue 7, 2015

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.

Graphical abstract: Exploring the scope of the isothiourea-mediated synthesis of dihydropyridinones

Supplementary files

Article information

Article type
Paper
Submitted
14 Nov 2014
Accepted
02 Dec 2014
First published
02 Jan 2015

Org. Biomol. Chem., 2015,13, 2177-2191

Exploring the scope of the isothiourea-mediated synthesis of dihydropyridinones

P. Yeh, D. S. B. Daniels, C. Fallan, E. Gould, C. Simal, J. E. Taylor, A. M. Z. Slawin and A. D. Smith, Org. Biomol. Chem., 2015, 13, 2177 DOI: 10.1039/C4OB02408G

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