Exploring the scope of the isothiourea-mediated synthesis of dihydropyridinones

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.

Citation

Yeh , P-P , Daniels , D S B , Fallan , C , Gould , E R , Simal Fernandez , C , Taylor , J E , Slawin , A M Z & Smith , A D 2015 , ' Exploring the scope of the isothiourea-mediated synthesis of dihydropyridinones ' , Organic & Biomolecular Chemistry , vol. 13 , no. 7 , pp. 2177-2191 . https://doi.org/10.1039/c4ob02408g

Publication

Organic & Biomolecular Chemistry

Status

Peer reviewed

DOI

https://doi.org/10.1039/c4ob02408g

ISSN

1477-0520

Type

Journal article

Rights

© 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

Description

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.

Collections

University of St Andrews Research

URI

http://hdl.handle.net/10023/7877