This work was supported by the Tatematsu Foundation. We are grateful to Zeon Co. for a gift of cyclopentyl methyl ether.
Catalytic Enantioselective Protonation of α-Oxygenated Ester Enolates Prepared through Phospha-Brook Rearrangement†
Article first published online: 31 JAN 2011
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 50, Issue 10, pages 2249–2252, March 1, 2011
How to Cite
Hayashi, M. and Nakamura, S. (2011), Catalytic Enantioselective Protonation of α-Oxygenated Ester Enolates Prepared through Phospha-Brook Rearrangement. Angew. Chem. Int. Ed., 50: 2249–2252. doi: 10.1002/anie.201007568
- Issue published online: 24 FEB 2011
- Article first published online: 31 JAN 2011
- Manuscript Received: 2 DEC 2010
- Tatematsu Foundation
- phospha-Brook rearrangement;
Phosphonates go chiral: The organocatalytic enantioselective reaction of α-ketoesters with phosphites using cinchona alkaloids and Na2CO3 has afforded α-phosphonyloxy esters with high enantioselectivities (see scheme). This process allows the formation of both enantiomers of the product. A catalyst loading of as low as 2 mol % does not result in a significant decrease of the enantioselectivity.