Acylative kinetic resolution of racemic heterocyclic amines with (R)-2-phenoxypropionyl chloride

被引：13
|
作者：
Vakarov, Sergey A. [1 ]
Gruzdev, Dmitry A. [1 ]
Chulakov, Evgeny N. [1 ]
Sadretdinova, Liliya Sh. [1 ]
Tumashov, Andrey A. [1 ]
Pervova, Marina G. [1 ]
Ezhikova, Marina A. [1 ]
Kodess, Mikhail I. [1 ,2 ]
Levit, Galina L. [1 ]
Krasnov, Victor P. [1 ]
Charushin, Valery N. [1 ,2 ]
机构：
[1] RAS, Postovsky Inst Organ Synth, Ural Branch, 22-20 S Kovalevskoy Akad Skaya St, Ekaterinburg 620990, Russia
[2] Ural Fed Univ, 19 Mira St, Ekaterinburg 620002, Russia
来源：
TETRAHEDRON-ASYMMETRY | 2016年 / 27卷 / 24期
基金：
俄罗斯科学基金会;
关键词：
DIASTEREOSELECTIVE ACYLATION; N-TOSYL-(S)-PROLYL CHLORIDE; EFFICIENT;
D O I：
10.1016/j.tetasy.2016.10.004
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The acylative kinetic resolution of racemic heterocyclic amines such as 3,4-dihydro-3-methyl-2H-[1,4] benzoxazines, 3,4-dihydro-3-methyl-2H-[1,4]benzothiazine, 2-methyl-1,2,3,4-tetrahydro-quinolines and 2-methylindoline with enantiopure (R)-2-phenoxypropionyl chloride has been studied. It has been found that acylation of 3,4-dihydro-3-methyl-2H-[1,4]benzothiazine proceeds with the best stereoselectively when compared with other racemic amines. An efficient method for the preparation of (S)-3,4-dihydro-3-methyl-2H-[1,4]benzothiazine (99.4% ee) via a kinetic resolution protocol was developed. The possibility of recycling (R)-2-phenoxypropionic acid has been demonstrated. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1231 / 1237
页数：7
相关论文
共 50 条
  • [41] Evaluating polymer-supported isothiourea catalysis in industrially-preferable solvents for the acylative kinetic resolution of secondary and tertiary heterocyclic alcohols in batch and flow
    Guha, Nitul Ranjan
    Neyyappadath, Rifahath M.
    Greenhalgh, Mark D.
    Chisholm, Ross
    Smith, Samuel M.
    McEvoy, Megan L.
    Young, Claire M.
    Rodriguez-Escrich, Carles
    Pericas, Miquel A.
    Hahner, Georg
    Smith, Andrew D.
    GREEN CHEMISTRY, 2018, 20 (19) : 4537 - 4546
  • [42] Kinetic resolution of amines by (R)-selective omega-transaminase from Mycobacterium vanbaalenii
    Shin, Giyoung
    Mathew, Sam
    Yun, Hyungdon
    JOURNAL OF INDUSTRIAL AND ENGINEERING CHEMISTRY, 2015, 23 : 128 - 133
  • [43] Biosynthesis of (R)-epichlorohydrin at high substrate concentration by kinetic resolution of racemic epichlorohydrin with a recombinant epoxide hydrolase
    Jin, Huo-Xi
    Liu, Zhi-Qiang
    Hu, Zhong-Ce
    Zheng, Yu-Guo
    ENGINEERING IN LIFE SCIENCES, 2013, 13 (04): : 385 - 392
  • [44] Amidase catalyzed kinetic resolution of racemic mandelamide to (R)- mandelate by Delftia tsuruhatensis ZJB-05174
    Zheng, Ren-chao
    Zheng, Yu-guo
    Shen, Yin-chu
    JOURNAL OF BIOTECHNOLOGY, 2008, 136 : S368 - S368
  • [45] Screening for enantioselective nitrilases:: kinetic resolution of racemic mandelonitrile to (R)-(-)-mandelic acid by new bacterial isolates
    Kaul, P
    Banerjee, A
    Mayilraj, S
    Banerjee, UC
    TETRAHEDRON-ASYMMETRY, 2004, 15 (02) : 207 - 211
  • [46] Kinetic resolution of racemic 2H-azirine via an asymmetric imine amidation
    Hu, Haipeng
    Liu, Xiaohua
    Feng, Xiaoming
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
  • [47] A way for resolution of (R, S)-2-octanol by combining dynamic kinetic resolution with double kinetic resolution
    Cong, FD
    Wang, YH
    Ma, CY
    Yu, HF
    Han, SP
    Tao, J
    Cao, SG
    ENZYME AND MICROBIAL TECHNOLOGY, 2005, 36 (04) : 595 - 599
  • [48] Unprecedented, fully recyclable, solid-supported reagent for the kinetic resolution of racemic amines through enantioselective N-acetylation
    Arseniyadis, S
    Subhash, PV
    Valleix, A
    Wagner, A
    Mioskowski, C
    CHEMICAL COMMUNICATIONS, 2005, (26) : 3310 - 3312
  • [49] The Kinetic Resolution of Racemic Amines Using a Whole-Cell Biocatalyst Co-Expressing Amine Dehydrogenase and NADH Oxidase
    Jeon, Hyunwoo
    Yoon, Sanghan
    Ahsan, Md Murshidul
    Sung, Sihyong
    Kim, Geon-Hee
    Sundaramoorthy, Uthayasuriya
    Rhee, Seung-Keun
    Yun, Hyungdon
    CATALYSTS, 2017, 7 (09):
  • [50] KINETIC RESOLUTION IN THE REACTION OF (2R,3R)-2,3-DIACETOXY-SUCCINIC AND (2R,3R)-2,3-DIBENZOYLOXY-SUCCINIC ANHYDRIDES WITH RACEMIC ALCOHOLS
    BELL, KH
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1979, 32 (01) : 65 - 70
12345