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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
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Asymmetric transfer hydrogenation of acetophenone derivatives with novel chiral phosphinite based η 6- p-cymene/ruthenium(II) catalysts
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Murat Aydemir
,
Nermin Meric
,
Akin Baysal
,
Yilmaz Turgut
,
Cezmi Kayan
,
Sevil Şeker
,
Mahmut Toğrul
,
Bahattin Gümgüm
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
DOI:
10.1016/j.jorganchem.2010.12.027
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