The authors acknowledge the Netherlands Organization for Scientific Research (NWO-VIDI (700.57.428, W.R.B.), Catchbio (J.J.D., M.F.M., B.L.F.), NRSC-C (B.L.F.), and ERC (279549, W.R.B.).
Palladium-Catalyzed Selective Anti-Markovnikov Oxidation of Allylic Esters†
Article first published online: 16 APR 2013
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 52, Issue 21, pages 5561–5565, May 17, 2013
How to Cite
Dong, J. J., Fañanás-Mastral, M., Alsters, P. L., Browne, W. R. and Feringa, B. L. (2013), Palladium-Catalyzed Selective Anti-Markovnikov Oxidation of Allylic Esters . Angew. Chem. Int. Ed., 52: 5561–5565. doi: 10.1002/anie.201301809
- Issue published online: 10 MAY 2013
- Article first published online: 16 APR 2013
- Manuscript Received: 3 MAR 2013
- Netherlands Organization for Scientific Research. Grant Number: 700.57.428
- ERC. Grant Number: 279549
- allylic esters;
An aldol alternative: The palladium(II)-catalyzed anti-Markovnikov oxidation of allylic esters to aldehydes at room temperature provides a viable alternative to valuable cross aldol products. High regioselectivity towards the aldehyde product was achieved using the ester protecting group for the allylic alcohol. Rapid isomerization and the much higher rate of oxidation of the branched isomer result in the same product forming from both linear and branched allylic esters.