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Asymmetric transfer hydrogenation of acetophenone derivatives with novel chiral phosphinite based η 6- p-cymene/ruthenium(II) catalysts

Asymmetric transfer hydrogenation of acetophenone derivatives with novel chiral phosphinite based η 6- p-cymene/ruthenium(II) catalysts,10.1016/j.jorg

Asymmetric transfer hydrogenation of acetophenone derivatives with novel chiral phosphinite based η 6- p-cymene/ruthenium(II) catalysts  
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Enantioselective reduction of prochiral ketones to optically active secondary alcohols is an important subject in synthetic organic chemistry because the resulting chiral alcohols are extremely useful, biologically active compounds. The new chiral ligands (2R)-2-[benzyl{(2-((diphenylphosphanyl)oxy)ethyl)}amino]butyldiphenylphosphinite, 1 and (2R)-2-[benzyl{(2-((dicyclohexylphosphanyl)oxy)ethyl)}amino]butyldicyclohexylphosphinite, 2 and the corresponding ruthenium(II) complexes 3 and 4 have been prepared. The structures of these complexes have been elucidated by a combination of multinuclear NMR spectroscopy, IR spectroscopy and elemental analysis. 31P–{1H} NMR, DEPT, 1H–13C HETCOR or 1H–1H COSY correlation experiments were used to confirm the spectral assignments. These ruthenium(II)–phosphinite complexes have been used as catalysts for the asymmetric transfer hydrogenation of acetophenone derivatives. Under optimized conditions, aromatic ketones were reduced in good conversions and in moderate to good enantioselectivities (up to 85% ee).
Journal: Journal of Organometallic Chemistry - J ORGANOMET CHEM , vol. 696, no. 8, pp. 1541-1546, 2011
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