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An Efficient Stereoselective Total Synthesis of All Stereoisomers of the Antibiotic Thiamphenicol through Ruthenium‐Catalyzed Asymmetric Reduction by Dynamic Kinetic Resolution (Eur. J. Org. Chem. 27/2015)
Author(s) -
Perez Marc,
Echeverria PierreGeorges,
MartinezArripe Elsa,
Ez Zoubir Mehdi,
Touati Ridha,
Zhang Zhaoguo,
Genet JeanPierre,
Phansavath Phannarath,
Ayad Tahar,
RatovelomananaVidal Virginie
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201590076
Subject(s) - kinetic resolution , chemistry , enantioselective synthesis , thiamphenicol , transfer hydrogenation , asymmetric hydrogenation , ruthenium , stereoselectivity , combinatorial chemistry , catalysis , stereochemistry , total synthesis , derivative (finance) , organic chemistry , antibiotics , chloramphenicol , biochemistry , financial economics , economics
The cover picture shows how chemists, by the judicious choice of the catalytic system, can control the stereochemical outcome of the ruthenium‐catalyzed enantioselective reduction of an inexpensive and readily available racemic α‐amido‐β‐keto ester derivative. More particularly, a dynamic kinetic resolution (DKR) process, through either asymmetric hydrogenation (AH) or asymmetric transfer hydrogenation (ATH), allowed the formation of the essential syn or anti relationship of key amino alcohols leading to the synthesis of all four stereoisomers of the antibiotic thiamphenicol. Details are discussed in the article by T. Ayad, V. Ratovelomanana‐Vidal et al. on 5949 ff .