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Asymmetric ruthenium tricarbonyl cyclopentadienone complexes; synthesis and application to asymmetric hydrogenation of ketones.

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Title: Asymmetric ruthenium tricarbonyl cyclopentadienone complexes; synthesis and application to asymmetric hydrogenation of ketones.
Authors: Del Grosso, Alessandro1 (AUTHOR), Clarkson, Guy J.1 (AUTHOR), Wills, Martin1 (AUTHOR) m.wills@warwick.ac.uk
Source: Inorganica Chimica Acta. Oct2019, Vol. 496, pN.PAG-N.PAG. 1p.
Subjects: Asymmetric synthesis, Ruthenium, Transfer hydrogenation, Hydrogenation, Ketones, Dialkylzinc
Abstract: • Novel enantiomerically-pure ruthenium tricarbonyl cyclopentadienones are reported. • Complexes were prepared via the cyclisation of C2-symmetric dialkynes with Ru3(CO) 12. • The new catalysts are effective in the asymmetric hydrogenation of ketones. • The new catalysts are prepared via an operationally simple procedure. A series of enantiomerically-pure ruthenium tricarbonyl cyclopentadienone complexes were prepared via the cyclisation of C2-symmetric dialkynes with Ru 3 (CO) 12. Four complexes were characterised by X-ray crystallography and a hydride derivative of one of these was characterised. The complexes were tested in the asymmetric hydrogenation and transfer hydrogenation of acetophenone. Whilst the catalysts were active, acetophenone was reduced in low ee, however a reduction product of up to 46% ee could be obtained when a mild base (i Pr 2 NEt or pyridine) was added to the reaction. [ABSTRACT FROM AUTHOR]
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Database: Engineering Source
Description
Abstract:• Novel enantiomerically-pure ruthenium tricarbonyl cyclopentadienones are reported. • Complexes were prepared via the cyclisation of C2-symmetric dialkynes with Ru3(CO) 12. • The new catalysts are effective in the asymmetric hydrogenation of ketones. • The new catalysts are prepared via an operationally simple procedure. A series of enantiomerically-pure ruthenium tricarbonyl cyclopentadienone complexes were prepared via the cyclisation of C2-symmetric dialkynes with Ru 3 (CO) 12. Four complexes were characterised by X-ray crystallography and a hydride derivative of one of these was characterised. The complexes were tested in the asymmetric hydrogenation and transfer hydrogenation of acetophenone. Whilst the catalysts were active, acetophenone was reduced in low ee, however a reduction product of up to 46% ee could be obtained when a mild base (i Pr 2 NEt or pyridine) was added to the reaction. [ABSTRACT FROM AUTHOR]
ISSN:00201693
DOI:10.1016/j.ica.2019.119043