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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
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.201500661
Subject(s) - thiamphenicol , kinetic resolution , chemistry , ruthenium , enantioselective synthesis , stereoselectivity , combinatorial chemistry , catalysis , stereochemistry , resolution (logic) , transfer hydrogenation , antibiotics , organic chemistry , chloramphenicol , biochemistry , artificial intelligence , computer science
Thiamphenicol is a widely used antibiotic that exhibits activity against numerous Gram‐positive and Gram‐negative pathogens. Here, we describe the expedient synthesis of its four stereoisomers through a dynamic kinetic resolution that follows a ruthenium‐catalyzed asymmetric hydrogenation or a hydrogen transfer reaction as the key step.