SpinPHOX/Ir(I) Catalyzed Asymmetric Hydrogenation of (E)-2-(hydroxymethyl)-3-Arylacrylic Acids

doi:10.6023/A14040314

Abstract

Optically active 3-aryl-2-hydroxymethylpropionoic acids are highly useful chiral building blocks for the preparation of some drugs, but so far their asymmetric syntheses are still plagued by modest enantioselectivity and/or limited substrate scope. In the present study, the SpinPHOX/Ir(I) complexes (S,S)-1c and (R,S)-1e have been demonstrated to be highly effective for the asymmetric hydrogenation of (E)-2-(hydroxymethyl)-3-arylacrylic acids, affording the corresponding optically active 3-aryl-2-hydroxymethylpropionoic acids in good to excellent enantiopurities (ee up to 95%). Catalyst screening and reaction optimization with (E)-2-(hydroxymethyl)-3-phenylacrylic acid 2a as the model substrate, revealed that the asymmetric hydrogenation was best conducted in dichloromethane at r.t. under 10 atm of hydrogen with (S,S)-1c as the catalyst, and the presence of 1 equiv. of a suitable organic base (such as triethylamine) was essential for full substrate conversion and excellent product enantioselectivity (94% ee). Evaluation of the substrate scope of the protocol was performed using various 2-hydroxymethyl cinnamic acid derivatives 2a～2n with various substituents on the phenyl group. Full conversions and good to high ee values were obtained in most cases, irrespective of the electron-withdrawing or -donating nature of the substituent. Using complex (R,S)-1e as the catalyst under a slightly modified reaction conditions (50 atm H₂, 40 ℃), several substrates were hydrogenated in excellent ee values but with the sense of chiral induction opposite to those obtained by using (S,S)-1c. The reaction can be readily scaled up to gram-scale with retention of enantioselectivity. Among the optically enriched hydrogenation products obtained from this procedure, (S)-3a, (R)-3a and (-)-3n can be used as chiral building blocks for the asymmetric synthesis of pharmaceuticals Alvimopan, Ecadotril, and Fasidotril, respectively. Using this protocol, various (E)-2-(hydroxymethyl)-3-arylacrylic acids could be readily hydrogenated in high optical purities, thus providing a facile access to both enantiomers of the chiral 3-aryl-2-hydroxymethylpropionoic acids as well as the relevant chiral drugs.

Key words: iridium(I), SpinPHOX ligands, asymmetric catalysis, hydrogenation, (E)-2-(hydroxymethyl)-3-arylacrylic acid, 2-hydroxymethyl-3-arylpropionic acid

Cite this article

Liu Xu, Han Zhaobin, Wang Zheng, Ding Kuiling. SpinPHOX/Ir(I) Catalyzed Asymmetric Hydrogenation of (E)-2-(hydroxymethyl)-3-Arylacrylic Acids[J]. Acta Chimica Sinica, 2014, 72(7): 849-855.

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SpinPHOX/Ir(I)催化的2-羟甲基-3-芳基丙烯酸的不对称氢化