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Development of Bifunctional Thiourea Organocatalysts Derived from a Chloramphenicol Base Scaffold and their Use in the Enantioselective Alcoholysis of meso Cyclic Anhydrides
Author(s) -
Yan LinJie,
Wang HaiFeng,
Chen WenXue,
Tao Yuan,
Jin KaiJun,
Chen FenEr
Publication year - 2016
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201600228
Subject(s) - enantioselective synthesis , thiourea , bifunctional , chemistry , chloramphenicol , base (topology) , organocatalysis , catalysis , organic chemistry , combinatorial chemistry , mathematics , biochemistry , antibiotics , mathematical analysis
The synthesis of new chloramphenicol‐base‐derived thiourea organocatalysts, (1 S ,2 R )‐ 12 a – f and (1 R ,2 R )‐ 15 a – c , and their use in the enantioselective alcoholysis of meso ‐anhydrides are described. In particular, hemiesters afforded excellent enantioselectivities if low loadings of (1 S ,2 R )‐ 12 a – f were used. Almost no enantioselectivities were achieved with the use of (1 R ,2 R )‐ 15 a – c . This technique was used to synthesize ( R )‐(−)‐baclofen.