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Catalytic Asymmetric Hydrogenation of Ethyl 2‐(Benzo[ b ]thiophen‐5‐yl)‐2‐oxoacetate with Ru‐SunPhos in the Formal Synthesis of T‐588
Author(s) -
Li Xiaoming,
Ma Xin,
Li Wanfang,
Tao Xiaoming,
Meng Qinghua,
Fan Weizheng,
Zhang Zhaoguo
Publication year - 2011
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201100305
Subject(s) - chemistry , catalysis , enantioselective synthesis , recrystallization (geology) , asymmetric hydrogenation , medicinal chemistry , organic chemistry , combinatorial chemistry , stereochemistry , paleontology , biology
Application of catalytic asymmetric hydrogenation of ethyl 2‐(benzo[ b ]thiophen‐5‐yl)‐2‐oxoacetate for the formal synthesis of cognitive enhancer T‐588 is described. The hydrogenation was conducted under the catalysis of Ru‐SunPhos system with HCl as additive. Ethyl 2‐(benzo[ b ]thiophen‐5‐yl)‐2‐hydroxy‐acetate was obtained with 98.6% ee , which could be easily upgraded to 99.5% ee after a simple recrystallization and served as the key intermediate in the synthesis of T‐588.