The authors thank the Royal Society (A.D.S.) and the EU (IEF for C.S.) for funding, and the EPSRC Mass Spectrometry Service Centre.
Dihydropyridones: Catalytic Asymmetric Synthesis, N- to C-Sulfonyl Transfer, and Derivatizations†
Article first published online: 1 MAR 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 15, pages 3653–3657, April 10, 2012
How to Cite
Simal, C., Lebl, T., Slawin, A. M. Z. and Smith, A. D. (2012), Dihydropyridones: Catalytic Asymmetric Synthesis, N- to C-Sulfonyl Transfer, and Derivatizations. Angew. Chem. Int. Ed., 51: 3653–3657. doi: 10.1002/anie.201109061
- Issue published online: 4 APR 2012
- Article first published online: 1 MAR 2012
- Manuscript Received: 22 DEC 2011
- Royal Society
- asymmetric synthesis;
- Lewis bases;
Benzotetramisole (1) promotes the reaction of ammonium enolates derived from arylacetic acids with N-tosyl-α,β-unsaturated ketimines, thus giving dihydropyridones with high diastereo- and enantiocontrol (see scheme). These products readily undergo N- to C-sulfonyl photoisomerization and are derivatized to afford stereodefined piperidines and tetrahydropyrans.