Nonenzymatic Acylative Kinetic Resolution of Racemic Amines and Related Compounds

被引:86
|
作者
Krasnov, Victor P. [1 ]
Gruzdev, Dmitry A. [1 ]
Levit, Galina L. [1 ]
机构
[1] RAS, Postovsky Inst Organ Synth, Ekaterinburg 620990, Russia
基金
俄罗斯基础研究基金会;
关键词
Kinetic resolution; Acylation; Amines; Amides; ENANTIOSELECTIVE ACYL TRANSFER; PLANAR-CHIRAL DERIVATIVES; BETA-HYDROXY AMINES; ENANTIOMERIC EXCESS; ABSOLUTE-CONFIGURATION; ASYMMETRIC-SYNTHESIS; SECONDARY ALCOHOLS; NUCLEOPHILIC CATALYSIS; SEC-ALCOHOLS; 1-SUBSTITUTED 3-AMINO-1,2-DICARBA-CLOSO-DODECABORANES;
D O I
10.1002/ejoc.201101489
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Acylative kinetic resolution of racemic amines occupies a highly important place among the methods for preparation of enantio enriched or pure amines. Nonenzymatic acylative kinetic resolution is usually carried out in the presence of chiral acyl-transfer catalysts or under the action of chiral enantio- or diastereoselective resolving agents. Recently, this line of investigations has been rapidly developed and very interesting results of design and synthetic application of both new catalysts and chiral acylating agents have been obtained. This microreview summarizes the recent advances in this area.
引用
收藏
页码:1471 / 1493
页数:23
相关论文
共 50 条
  • [21] Efficient kinetic resolution of racemic amines using a transaminase in combination with an amino acid oxidase
    Truppo, Matthew D.
    Turner, Nicholas J.
    Rozzell, J. David
    CHEMICAL COMMUNICATIONS, 2009, (16) : 2127 - 2129
  • [22] N-Tosyl-(S)-Prolyl Chloride in Kinetic Resolution of Racemic Heterocyclic Amines
    Gruzdev, D. A.
    Vakarov, S. A.
    Levit, G. L.
    Krasnov, V. P.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2014, 49 (12) : 1795 - 1807
  • [23] Kinetic resolution of racemic amines using provisional molecular chirality generated by spontaneous crystallization
    Sakamoto, Masami
    Fujita, Kazuyuki
    Yagishita, Fumitoshi
    Unosawa, Atsushi
    Mino, Takashi
    Fujita, Tsutomu
    CHEMICAL COMMUNICATIONS, 2011, 47 (14) : 4267 - 4269
  • [24] Kinetic Resolution of Racemic Primary Amines Using Geobacillus stearothermophilus Amine Dehydrogenase Variant
    Tseliou, Vasilis
    Knaus, Tanja
    Vilim, Jan
    Masman, Marcelo F.
    Mutti, Francesco G.
    CHEMCATCHEM, 2020, 12 (08) : 2184 - 2188
  • [25] N-Tosyl-(S)-Prolyl Chloride in Kinetic Resolution of Racemic Heterocyclic Amines
    D. A. Gruzdev
    S. A. Vakarov
    G. L. Levit
    V. P. Krasnov
    Chemistry of Heterocyclic Compounds, 2014, 49 : 1795 - 1807
  • [26] Kinetic Resolution of Racemic Amines to Enantiopure (S)-amines by a Biocatalytic Cascade Employing Amine Dehydrogenase and Alanine Dehydrogenase
    Patil, Mahesh D.
    Yoon, Sanghan
    Jeon, Hyunwoo
    Khobragade, Taresh P.
    Sarak, Sharad
    Pagar, Amol D.
    Won, Yumi
    Yun, Hyungdon
    CATALYSTS, 2019, 9 (07):
  • [27] Acylative kinetic resolution of racemic aromatic β-hydroxy esters catalyzed by chiral nucleophilic N-(1-arylethyl)benzoguanidines
    Yamada, Akira
    Nakata, Kenya
    Shiina, Isamu
    TETRAHEDRON-ASYMMETRY, 2017, 28 (04) : 516 - 521
  • [28] STUDIES TOWARDS THE N-ACYLATIVE KINETIC RESOLUTION OF NOBIN
    Arseniyadis, Stellios
    Mahesh, Mohan
    McDaid, Paul
    Hampel, Thomas
    Davey, Stephen G.
    Spivey, Alan C.
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2011, 76 (10) : 1239 - 1253
  • [29] Impact of the Difluoromethylene Group in the Organocatalyzed Acylative Kinetic Resolution of α,α-Difluorohydrins
    Desrues, Titouan
    Merad, Jeremy
    Andrei, Daniela
    Pons, Jean-Marc
    Parrain, Jean-Luc
    Medebielle, Maurice
    Quintard, Adrien
    Bressy, Cyril
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (47) : 24924 - 24929
  • [30] Nonenzymatic Kinetic Resolution of Secondary Alcohols
    Organic Chemistry 2, Ctr. for Chem. and Chem. Engineering, University of Lund, P.O. Box 124, S-221 00 Lund, Sweden
    Angew Chem (Int Ed Engl), 24 (2731-2733):