Enantioselective Synthesis of anti-β-Hydroxy-α-Amido Esters by Asymmetric Transfer Hydrogenation in Emulsions
2012 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 18, no 23, 2719-2723 p.Article in journal (Refereed) Published
Herein, we present two methods for an asymmetric transfer hydrogenation through the dynamic kinetic resolution of α-amido-β-ketoesters. These procedures yield the corresponding anti-β-hydroxy-α-amido esters in good yields and with good diastereo- and enantioselectivities. First, the scope of the reduction of α-amido-β-ketoesters by using triethylammonium formate azeotrope is examined. Then, an emulsion technology with sodium formate is explored, which allows for broader substrate scope, faster reaction times, and lower catalyst loading. Furthermore, these reactions are operationally simple and can be set up in air.
Place, publisher, year, edition, pages
2012. Vol. 18, no 23, 2719-2723 p.
amino acids, asymmetric synthesis, emulsions, kinetic resolution, transfer hydrogenation
IdentifiersURN: urn:nbn:se:kth:diva-96516DOI: 10.1002/chem.201103739ISI: 000304438000026ScopusID: 2-s2.0-84861634727OAI: oai:DiVA.org:kth-96516DiVA: diva2:531031
FunderKnut and Alice Wallenberg FoundationSwedish Research Council
QC 201206052012-06-052012-06-052012-06-26Bibliographically approved