• 中国精品科技期刊
  • 中国高校百佳科技期刊
  • 中国中文核心期刊
  • 中国科学引文数据库核心期刊
Advanced Search
CHEN Haitao, LU Xiaofei, HAN Fujiao, WANG Wenxin, FU Jingguo, CHEN Hui. Asymmetric hydrogenation of methyl-2-acylamino-3-arylacrylate[J]. Journal of China Pharmaceutical University, 2018, 49(5): 553-557. DOI: 10.11665/j.issn.1000-5048.20180506
Citation: CHEN Haitao, LU Xiaofei, HAN Fujiao, WANG Wenxin, FU Jingguo, CHEN Hui. Asymmetric hydrogenation of methyl-2-acylamino-3-arylacrylate[J]. Journal of China Pharmaceutical University, 2018, 49(5): 553-557. DOI: 10.11665/j.issn.1000-5048.20180506

Asymmetric hydrogenation of methyl-2-acylamino-3-arylacrylate

More Information
  • By using(S)-MonoPHOS and [Rh(COD)2]BF4 as catalyst, the asymmetric hydrogenation reactions of methyl-2-acylamino-3-arylacrylate and the effect of different amino protective groups on hydrogenation efficacy were studied. The products resulting from asymmetric hydrogenation were hydrolyzed by hydrochloric acid, and the corresponding amino acids were obtained at yields of 63%- 92%.
  • [1]
    Zhang JL,Jin W,Wang XQ,et al.A novel octreotide modified lipid vesicle improved the anticancer efficacy of doxorubicin in somatostatin receptor 2 positive tumormodels[J].Mol Pharm,2010,7(4):1159-1168.
    [2]
    Daisuke T,Seiichi N,Satoji T.Process for producing nateglinide crystals:WO,2002032854 [P].2002-04-25[2018-09-10] .
    [3]
    Chen X,Rao JA,Wang J,et al.A facile enantioseparation for amino acids enantiomers using β-cyclodextrins functionalized Fe3O4 nanospheres[J].Chem Commun,2011,47(37):10317-10319.
    [4]
    Bae H,Lee S,Hong S,et al.Production of aromatic d-amino acids from α-keto acids and ammonia by coupling of four enzyme reactions[J].J Mol Catal B:Enzym,1999,6(3):241-247.
    [5]
    Genet J.Asymmetric catalytic hydrogenation design of new Ru catalysts and chiral ligands:from laboratory to industrial applications[J].Acc Chem Res,2003,36(12):908-918.
    [6]
    Etayo P,Vidal-Ferran A.Rhodium-catalysed asymmetric hydrogenation as a valuable synthetic tool for the preparation of chiral drugs[J].Chem Soc Rev,2013,42(2):728-754.
    [7]
    Van den Berg M,Minnaard AJ,Haak RM,et al.Monodentate phosphoramidites:a breakthrough in rhodium-catalysed asymmetric hydrogenation of olefins[J].Adv Synth Catal,2003,345(1/2):308-323.
    [8]
    Jursic BS,Sagiraju S,Ancalade DK,et al.Practical preparation of Z-α-(N-Acetylamino)-and Z-α-(N-Benzoylamino)-α,β-unsaturated acids[J].Synth Commun,2007,37(10):1709-1714.
    [9]
    Cleary T,Brice J,Kennedy N,et al.One-pot process to Z-α-benzoylamino-acrylic acid methyl esters via potassium phosphate-catalyzed Erlenmeyer reaction[J].Tetrahedron Lett,2010,51(4):625-628.
    [10]
    Hulst R,de Vries NK,Feringa BL.α-Phenylethylamine based chiral phospholidines;new agents for the determination of the enantiomeric excess of chiral alcohols,amines and thiols by means of 31P NMR[J].Tetrahedron:Asymmetry,1994,5(4):699-708.
    [11]
    Yu LT,Wang Z,Wu J,et al.Directed orthogonal self-assembly of homochiral coordination polymers for heterogeneous enantioselective hydrogenation[J].Angew Chem Int Ed,2010,49(21):3627-3630.
    [12]
    Tomita K,Oishi S,Ohno H,et al.Structure-activity relationship study and NMR analysis of fluorobenzoyl pentapeptide GPR54 agonists[J].Biopolymers,2008,90(4):503-511.
    [13]
    Murray G,Debra M,Pedro RR,et al.Beta-adrenergic antagonist compounds and derivatives of beta-adrenergic antagonists:EP,117089 A1[P].1984-08-29[2018-09-10] .
    [14]
    Evans DA,Michael FE,Tedrow JS,et al.Application of chiral mixed phosphorus/sulfur ligands to enantioselective rhodium-catalyzed dehydroamino acid hydrogenation and ketone hydrosilylation processes[J].J Am Chem Soc,2003,125(12):3534-3543.
    [15]
    Navarre L,Martinez R,Genet J,et al.Access to enantioenriched α-amino esters via rhodium-catalyzed 1,4-addition/enantioselective protonation[J].J Am Chem Soc,2008,130(19):6159-6169.
    [16]
    Rao PN,Peterson DM,Acosta CK,et al.Synthesis of cis and trans-4-aminocyclohexyl-D-alanine derivatives and determination of their sterochemistry[J].Org Prep Proced Int,1991,23(1):103-110.
    [17]
    Lander PA,Hegedus LS.Asymmetric synthesis of α-amino acids by copper-catalyzed conjugate addition of grignard reagents to optically active carbamatoacrylates[J].J Am Chem Soc,1994,116(18):8126-8132.
    [18]
    Pirrung MC,Krishnamurthy N.Preparation of(R)-phenylalanine analogs by enantioselective destruction using L-amino acid oxidase[J].J Org Chem,1993,58(4):957-958.
    [19]
    Fitzi R,Seebach D.Resolution and use in α-amino acid synthesis of imidazolidinone glycine derivatives[J].Tetrahedron,1988,44(17):5277-5292.
  • Related Articles

    [1]DENG Zhen, HUANG Wei, WANG Xiaoqin. Effects of Pseudomonas aeruginosa PmrB△Leu172 mutation on polymyxin B resistance[J]. Journal of China Pharmaceutical University, 2024, 55(6): 809-815. DOI: 10.11665/j.issn.1000-5048.2023121001
    [2]SHI Min, YONG Qin, HE Yingna, HUANG Shiqin, ZHAO Xuan, YU Xian. Construction and in vivo evaluation of a thermosensitive hydrogel system loading with Pseudomonas aeruginosa DNA vaccine[J]. Journal of China Pharmaceutical University, 2021, 52(2): 186-194. DOI: 10.11665/j.issn.1000-5048.20210207
    [3]HUANG Shiqin, SHI Min, HE Yingna, YUE Hanxun, YU Xian. Construction and in vitro evaluation of DC-targeted aptamer-modified Pseudomonas aeruginosa DNA vaccine delivery system[J]. Journal of China Pharmaceutical University, 2019, 50(6): 743-752. DOI: 10.11665/j.issn.1000-5048.20190616
    [4]WU Mingming, FANG Lei, GOU Shaohua, CHEN Li. 以2-甲基-2-取代苯氧基丙酸为离去基团的铂(Ⅱ)配合物的合成、表征及细胞毒活性[J]. Journal of China Pharmaceutical University, 2013, 44(4): 303-306. DOI: 10.11665/j.issn.1000-5048.20130403
    [5]Cloning of D-hydantoinaseGene from Pseudomonas and Its Expression in E.coli[J]. Journal of China Pharmaceutical University, 2001, (3): 69-72.
    [6]Dual-enzymatic Synthesis of D-(-)-p-Hydrox yphenylglycine[J]. Journal of China Pharmaceutical University, 2001, (2): 75-78.
    [8]Chemoenzymatic Synthesis of D p Hydroxyphenylgycine[J]. Journal of China Pharmaceutical University, 1998, (5): 74-76.
    [9]Xu Jiyang, Wu Wutong, Jin Shenghao, Yao Wenbin. Chemico-Enzymatic Synthesis of Sweetener Aspartame[J]. Journal of China Pharmaceutical University, 1994, (1).
    [10]Synthesis of 1,2,3,4,4a,5-Hexahydro-10-H-Dibenzo [a,d]-Cycloheptatriene-10-One[J]. Journal of China Pharmaceutical University, 1992, (5): 260-262.

Catalog

    Article views (628) PDF downloads (959) Cited by()

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return