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Amine‐Tunable Ruthenium Catalysts for Asymmetric Reduction of Ketones
Author(s) -
Rodríguez Sonia,
Qu Bo,
Fandrick Keith R.,
Buono Frederic,
Haddad Nizar,
Xu Yibo,
Herbage Melissa A.,
Zeng Xingzhong,
Ma Shengli,
Grinberg Nelu,
Lee Heewon,
Han Zhengxu S.,
Yee Nathan K.,
Senanayake Chris H.
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300727
Subject(s) - chemistry , ruthenium , transfer hydrogenation , noyori asymmetric hydrogenation , enantioselective synthesis , asymmetric hydrogenation , catalysis , diamine , phosphine , amine gas treating , aryl , combinatorial chemistry , alkyl , chirality (physics) , organic chemistry , chiral symmetry breaking , quark , nambu–jona lasinio model , physics , quantum mechanics
A series of efficient ruthenium catalysts has been developed for the asymmetric hydrogenation and transfer hydrogenation of ketones with high reactivities and selectivities. The new chiral bisdihydrobenzooxaphosphole (BIBOP)/diamine‐ruthenium complexes catalyzed the enantioselective hydrogenation of substrates such as aryl and heteroaryl cyclic and alkyl ketones with substrate/catalyst (S/C) ratios of up to 100,000. The opposite sense of enantioselectivity can be obtained by proper selection of a diamine with a given chirality of the phosphine. The usefulness of the new system has been demonstrated in the asymmetric hydrogenation of a complex synthetic intermediate towards cholesteryl ester transfer protein (CETP) inhibitors at S/C 20,000 on large‐scale operation.