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- Title
Amine-Tunable Ruthenium Catalysts for Asymmetric Reduction of Ketones.
- Authors
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.
- Abstract
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.
- Subjects
RUTHENIUM catalysts; HYDROGENATION; KETONES; CHOLESTERYL ester transfer protein; CHIRALITY; PHOSPHINE
- Publication
Advanced Synthesis & Catalysis, 2014, Vol 356, Issue 2/3, p301
- ISSN
1615-4150
- Publication type
Article
- DOI
10.1002/adsc.201300727