The first enantiomerically pure synthesis of (S)- and (R)-Naftopidil utilizing Hydrolytic Kinetic Resolution of (±)-(α-naphthyl) glycidyl ether

被引:10
|
作者
Kothakonda, KK [1 ]
Bose, DS
机构
[1] Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada
[2] Chem Ind Inst Toxicol, Fine Chem Lab, Hyderabad, Andhra Pradesh, India
关键词
D O I
10.1246/cl.2004.1212
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Hydrolytic Kinetic Resolution (HKR) of (+/-)-(alpha-Naphthyl) glycidyl ether with (R,R)-salen Co(III) OAc complex provided enatiomerically pure (S)-naphthyl glycidyl ether and (R)-1-naphthyl glycerol; opening of the corresponding pure terminal epoxide with 1-(2-methoxyphenyl)piperizine gave the enantiomerically pure (S)- and (R)-Naftopidil.
引用
收藏
页码:1212 / 1213
页数:2
相关论文
共 50 条
  • [41] First practical synthesis of enantiomerically pure (R)- and (S)-desmethylsibutramine (DMS) and unambiguous determination of their absolute configuration by single-crystal X-ray analysis
    Han, ZX
    Krishnamurthy, D
    Pflum, D
    Fang, QK
    Butler, H
    Cameron, TS
    Wald, SA
    Senanayake, CH
    TETRAHEDRON-ASYMMETRY, 2002, 13 (02) : 107 - 109
  • [42] Chiral auxiliaries with a switching center:: New tools in asymmetric synthesis.: Application to the synthesis of enantiomerically pure (R)- and (S)-α-amino acids
    Meyer, L
    Poirier, JM
    Duhamel, P
    Duhamel, L
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23): : 8094 - 8095
  • [43] Efficient synthesis of enantiomerically pure (S)-δ-azaproline starting from (R)-α-hydroxy-γ-butyrolactone via the Mitsunobu reaction
    Voss, Emelyne
    Arrault, Axelle
    Bodiguel, Jacques
    Jamart-Gregoire, Brigitte
    TETRAHEDRON-ASYMMETRY, 2009, 20 (15) : 1809 - 1812
  • [44] Synthesis of the Neurokinin 1 Receptor Antagonist (+)-L-733,060 by Jacobsen’s Hydrolytic Kinetic Resolution
    D. N. Bhangare
    V. B. Mahale
    R. G. Shinde
    M. D. Nikalje
    S. D. Duthade
    M. N. Lokhande
    Russian Journal of Organic Chemistry, 2020, 56 : 2159 - 2164
  • [45] Synthesis of the Neurokinin 1 Receptor Antagonist (+)-L-733,060 by Jacobsen's Hydrolytic Kinetic Resolution
    Bhangare, D. N.
    Mahale, V. B.
    Shinde, R. G.
    Nikalje, M. D.
    Duthade, S. D.
    Lokhande, M. N.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (12) : 2159 - 2164
  • [46] SYNTHESIS OF ENANTIOMERICALLY PURE (S)-(+)-3-HYDROXYTETRAHYDROFURAN AND ITS R-ENANTIOMER FROM MALIC OR TARTARIC ACID
    TANDON, VK
    VANLEUSEN, AM
    WYNBERG, H
    JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (16): : 2767 - 2769
  • [47] Efficient and Practical Syntheses of Enantiomerically Pure (S)-(-)-Norcryptostyline I, (S)-(-)-Norcryptostyline II, (R)-(+)-Salsolidine and (S)-(-)-Norlaudanosine via a Resolution-Racemization Method
    Zhu, Ruiheng
    Xu, Zhangli
    Ding, Wei
    Liu, Shiling
    Shi, Xiaoxin
    Lu, Xia
    CHINESE JOURNAL OF CHEMISTRY, 2014, 32 (10) : 1039 - 1048
  • [48] First Enantioselective Synthesis of Surinamensinol B and a Non-Natural Polysphorin Analogue by a Two-Stereocentered Hydrolytic Kinetic Resolution
    Lalwani, Komal G.
    Sudalai, Arumugam
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (33) : 7344 - 7351
  • [49] Synthesis of enantiomerically pure C2-symmetric 4-pyrrolidinopyridine derivative as a chiral acyl transfer catalyst for the kinetic resolution of secondary alcohols
    Naraku, G
    Shimomoto, N
    Hanamoto, T
    Inanaga, J
    ENANTIOMER, 2000, 5 (01): : 135 - 138
  • [50] Synthesis of optically pure terminal epoxide and 1,2-diol via hydrolytic kinetic resolution catalyzed by new heterometallic salen complexes
    Thakur, Santosh Singh
    Chen, Shu-Wei
    Li, Wenji
    Shin, Chang-Kyo
    Koo, Yoon-Mo
    Kim, Geon-Joong
    SYNTHETIC COMMUNICATIONS, 2006, 36 (16) : 2371 - 2383