Novel Dendritic Ligands of Chiral 1,2-Diamine and Their Application in Asymmetric Hydrogenation of Simple Aryl Ketones

Abstract

Novel dendritic chiral vicinal diamine ligands have been synthesized and a series of dendritic Ru(BINAP)(diamine) catalysts were developed for asymmetric hydrogenation of a variety of ­simple aryl ketones in good catalytic activity and high enantioselectivity, as well as facile catalyst recycling. An increase of enantio­selectivities was obtained by using the dendritic catalysts compared with Noyori catalysts under the same conditions in the case of ­several substrates. Meanwhile, a remarkable structural effect on ­catalytic activity and enantioselectivity, as well as reuse was ­observed.

Key words

chiral 1,2-diamine - dendritic ligand - ruthenium complex - asymmetric hydrogenation

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12

ESI-HRMS data for the dendritic ligands.
Ligand (S,S)-7a: m/z calcd for C₂₈H₂₈N₂O₂: 424.2151; found: 424.1915.
Ligand (S,S)-7b: m/z calcd for C₅₆H₅₄KN₂O₆ [M + K + 2 H]: 889.3619; found: 889.4199; C₅₆H₅₀NO₆ [M - NH₂]: 832.3638; found: 832.3673.
Ligand (S,S)-7c: m/z calcd for C₁₁₂H₁₀₁N₂NaO₁₄ [M + Na + H] (MALDI-TOF): 1719.7; found: 1720.1.
Ligand (S,S)-7d: m/z calcd for C₂₂₄H₂₀₃N₂NaO₃₀ [M + Na + 7 H] (MALDI-TOF): 3423.4: found: 3423.4.