A study on the induction of stereoselectivity in the Strecker synthesis of basic amino acid-derived α-amino nitriles

被引：4
|
作者：
Ventosa-Andres, Pilar [1 ]
Teresa Garcia-Lopez, M. [1 ]
Herranz, Rosario [1 ]
机构：
[1] CSIC, Inst Quim Med, E-28006 Madrid, Spain
来源：
TETRAHEDRON-ASYMMETRY | 2012年 / 23卷 / 15-16期
关键词：
MOLECULAR DIVERSITY; CCK-4; ANALOGS; SCAFFOLDS; KETIMINES; SYSTEM;
D O I：
10.1016/j.tetasy.2012.07.009
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Diverse basic amino acid-derived alpha-amino nitriles have been synthesized via a modified Strecker reaction, using TMSCN as the cyanide source. It has been found that this synthesis is a slow thermodynamically controlled reaction, where it was difficult to induce stereocontrol. Moderate selectivity was induced by thermodynamic control of the reaction in MeOH. The absolute configuration at the stereogenic center generated was assigned by chemical correlation with 2-oxopiperazine derivatives. (c) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1198 / 1205
页数：8
相关论文
共 50 条
  • [31] Plant amino acid-derived vitamins: biosynthesis and function
    Miret, Javier A.
    Munne-Bosch, Sergi
    AMINO ACIDS, 2014, 46 (04) : 809 - 824
  • [32] Amino Acid-Derived Bifunctional Phosphines for Enantioselective Transformations
    Wang, Tianli
    Han, Xiaoyu
    Zhong, Fangrui
    Yao, Weijun
    Lu, Yixin
    ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (07) : 1369 - 1378
  • [33] Thickening mechanisms for an amino acid-derived surfactant composition
    Trang Vu
    Koenig, Peter
    Cochran, Brooke M.
    Ananthapadmanabhan, K. P.
    Weaver, Mike
    Reeder, Bob
    Hutton, Howard D.
    Kasting, Gerald B.
    COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS, 2020, 589
  • [34] Supramolecular receptors from α-amino acid-derived lipids
    Hachisako, H
    Murata, Y
    Ihara, H
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, (11): : 2569 - 2577
  • [35] Amino acid-derived iodobenzene dicarboxylates: Reagents for oxidative conversion of alkenes to amino acid esters
    Koposov, AY
    Boyarskikh, VV
    Zhdankin, VV
    ORGANIC LETTERS, 2004, 6 (20) : 3613 - 3615
  • [36] Glycerol Mediated Strecker Reaction: Catalyst-free Protocol for the Synthesis of α-Amino Nitriles
    Ghogare, Ramesh S.
    Rajeshwari, K.
    Narsaiah, A. Venkat
    LETTERS IN ORGANIC CHEMISTRY, 2014, 11 (09) : 688 - 692
  • [37] Novel and efficient transformation of α-amino nitrile to α-imino and α-amide nitriles in asymmetric Strecker synthesis
    Namba, K
    Kawasaki, M
    Takada, I
    Iwama, S
    Izumida, M
    Shinada, T
    Ohfune, Y
    TETRAHEDRON LETTERS, 2001, 42 (22) : 3733 - 3736
  • [38] Study of Amino Acid-Derived 3-Acyltetramic Acids as Herbicidal Agents
    Backx, Simon
    Van Vooren, Jelle
    Geerts, Jasper
    Hyde, Cedric
    Van Hecke, Owen
    Pappaert, Hanne
    Dewitte, Kevin
    Ameye, Maarten
    Audenaert, Kris
    Desmedt, Willem
    Mangelinckx, Sven
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2024, 72 (36) : 19644 - 19656
  • [39] Synthesis and SAR of amino acid-derived heterocyclic progesterone receptor full and partial agonists
    Hammond, Marlys
    Patterson, Jaclyn R.
    Manns, Sharada
    Hoang, Tram H.
    Washburn, David G.
    Trizna, Walter
    Glace, Lindsay
    Grygielko, Eugene T.
    Nagilla, Rakesh
    Nord, Melanie
    Fries, Harvey E.
    Minick, Douglas J.
    Laping, Nicholas J.
    Bray, Jeffrey D.
    Thompson, Scott K.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (10) : 2637 - 2641
  • [40] CuAIOX catalyst for the batch-flow tandem synthesis of amino acid-derived furfurylamines
    Nuzhdin, Alexey L.
    Bukhtiyarova, Marina, V
    Eltsov, Ilia, V
    Bukhtiyarov, Valerii, I
    MENDELEEV COMMUNICATIONS, 2021, 31 (06) : 813 - 814
12345