Bifunctional Ammonium Salt Catalyzed Asymmetric α-Hydroxylation of β-Ketoesters by Simultaneous Resolution of Oxaziridines

Johanna Novacek; Joseph A Izzo; Mathew J Vetticatt; Mario Waser

doi:10.1002/chem.201604153

Bifunctional Ammonium Salt Catalyzed Asymmetric α-Hydroxylation of β-Ketoesters by Simultaneous Resolution of Oxaziridines

Chemistry. 2016 Nov 21;22(48):17339-17344. doi: 10.1002/chem.201604153. Epub 2016 Oct 20.

Authors

Johanna Novacek¹, Joseph A Izzo², Mathew J Vetticatt², Mario Waser¹

Affiliations

¹ Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstr. 69, 4040, Linz, Austria.
² Department of Chemistry, Binghamton University, Binghamton, New York, 13902, USA.

PMID: 27763714
DOI: 10.1002/chem.201604153

Abstract

Chiral bifunctional urea-containing ammonium salts were found to be very efficient catalysts for asymmetric α-hydroxylation reactions of β-ketoesters with oxaziridines under base-free conditions. The reaction is accompanied by a simultaneous kinetic resolution of the oxaziridine and a plausible and so far unprecedented bifunctional transition-state model has been obtained by means of DFT calculations.

Keywords: asymmetric catalysis; ion pairs; non-covalent interactions; resolution; transition-state model.