Asymmetric Hydrogenation of Aromatic Ketones Catalyzed by Achiral Monophosphine TPPTS-Stabilized Ru in PEG-Water

doi:10.3724/SP.J.1088.2011.10434

Abstract

Abstract: PEG-400 was found to be a green and recyclable reaction medium for asymmetric hydrogenation of aromatic ketones catalyzed by achiral monophosphine TPPTS (P(m-C₆H₄SO₃Na)₃), stabilized ruthenium modified by (1S,2S)-DPENDS (DPENDS: disodium salt of sulfonated (1S,2S)-1,2-diphenyl-1,2-ethylene-diamine). A 84.9% ee was obtained for acetophenone under the optimized conditions. The resulting products can be easily separated from the catalyst by extraction with n-hexane. The catalyst immobilized on PEG-400 not only exhibits excellent activity and enantioselectivity but also can be recycled and reused several times without loss of activity and enantioselectivity.

Key words: TPPTS-stabilized ruthenium, aromatic ketone, asymmetric hydrogenation, aromatic sec-alcohol, polyethylene glycol-400-water

QIN Rui-Xiang, WANG Jin-Bo, XIONG Wei, LIU De-Rong, FENG Jian, CHEN Hua. Asymmetric Hydrogenation of Aromatic Ketones Catalyzed by Achiral Monophosphine TPPTS-Stabilized Ru in PEG-Water[J]. Chinese Journal of Catalysis, 2011, 32(9): 1490-1495.

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