Amine‐Tunable Ruthenium Catalysts for Asymmetric Reduction of Ketones. Issue 2 (2nd February 2014)

• Record Type: Journal Article
• 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.
• Is Part Of: Advanced synthesis & catalysis. Volume 356:Issue 2/3(2014)
• Page Start: 301
• Page End: 307
• Publication Date: 2014-02-02
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201300727
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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.</p> <p> <boxed-text content-type="graphic" position="anchor" orientation="portrait"> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg4sr7qq2f" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </boxed-text> </p> </abstract>