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Enantioselective Synthesis of anti ‐β‐Hydroxy‐α‐Amido Esters by Asymmetric Transfer Hydrogenation in Emulsions
Author(s) -
SeashoreLudlow Brinton,
Villo Piret,
Somfai Peter
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201103739
Subject(s) - enantioselective synthesis , transfer hydrogenation , chemistry , sodium formate , kinetic resolution , substrate (aquarium) , azeotrope , yield (engineering) , catalysis , organic chemistry , formate , combinatorial chemistry , materials science , oceanography , geology , distillation , ruthenium , metallurgy
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.