2019•Advanced Synthesis & CatalysisRequires access

Enantioselective Synthesis of 2‐Hydroxyalkyl Diarylphosphinates by Ruthenium‐Catalyzed Asymmetric Transfer Hydrogenation

Kaili Zhang, Yuping Yang, Huan Liu, Qixing Liu, Jinliang Lv, Haifeng Zhou

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Abstract

Abstract An asymmetric transfer hydrogenation of 2‐oxo alkyl phosphinates in the presence of a chiral diamine ruthenium catalyst with HCOONa as a hydrogen source in aqueous 2,2,2‐trifluoroethanol under mild conditions gave a wide range of chiral 2‐hydroxyalkyl diarylphosphinates in enantiomeric excesses of 97–99% and in good yields. The absolute configuration of the products was determined to be R by single‐crystal X‐ray diffraction. magnified image

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Abstract An asymmetric transfer hydrogenation of 2‐oxo alkyl phosphinates in the presence of a chiral diamine ruthenium catalyst with HCOONa as a hydrogen source in aqueous 2,2,2‐trifluoroethanol under mild conditions gave a wide range of chiral 2‐hydroxyalkyl diarylphosphinates in enantiomeric excesses of 97–99% and in good yields. The absolute configuration of the products was determined to be R by single‐crystal X‐ray diffraction. magnified image

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Available abstract

Abstract An asymmetric transfer hydrogenation of 2‐oxo alkyl phosphinates in the presence of a chiral diamine ruthenium catalyst with HCOONa as a hydrogen source in aqueous 2,2,2‐trifluoroethanol under mild conditions gave a wide range of chiral 2‐hydroxyalkyl diarylphosphinates in enantiomeric excesses of 97–99% and in good yields. The absolute configuration of the products was determined to be R by single‐crystal X‐ray diffraction. magnified image

Key concepts: Chemistry, Enantioselective synthesis, Ruthenium, Transfer hydrogenation, Catalysis, Enantiomer, Noyori asymmetric hydrogenation, Diamine

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