The kinetic resolution of oxazinones by alcoholysis: access to orthogonally protected β-amino acids

被引:4
|
作者
Cronin, Sarah A. [1 ]
Connon, Stephen J. [1 ]
机构
[1] Trinity Coll Dublin, Trinity Biomed Sci Inst, Sch Chem, Dublin, Ireland
基金
爱尔兰科学基金会;
关键词
ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; MESO-ANHYDRIDES; ORGANOCATALYSTS; AZLACTONES; PEPTIDES; DESYMMETRIZATION; CYCLOADDITIONS; CISPENTACIN; DERIVATIVES;
D O I
10.1039/d1ob01306h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The catalytic, alcoholytic kinetic resolution of oxazinones is reported. A novel, stereochemically dense cinchona alkaloid-based catalyst can facilitate the highly enantiodiscriminatory (S up to 101) ring-opening of oxazinones equipped with electrophilic aryl units to generate orthogonally protected beta-amino acids for the first time.
引用
收藏
页码:7348 / 7352
页数:5
相关论文
共 50 条
  • [21] Preparation of novel ligands for the dynamic kinetic resolution of α-amino acids
    Allbritton, Elisabeth
    Bond, Abbagale
    Crone, Sarah
    Hicks, Elizabeth
    Kemp, Kenneth
    Tresp, David
    Widick, Devin
    Hamburger, Samantha
    Wright, Payton
    Ellis, Trevor
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
  • [22] Enhancing a Sphaerobacter thermophilus ω-transaminase for kinetic resolution of β- and γ-amino acids
    Wegner, Uwe
    Matthes, Falko
    von Wiren, Nicolaus
    Lemke, Ina
    Bode, Ruediger
    Vorbrodt, H. -Matthias
    Rauter, Marion
    Kunze, Gotthard
    AMB EXPRESS, 2023, 13 (01)
  • [23] Enhancing a Sphaerobacter thermophilus ω-transaminase for kinetic resolution of β- and γ-amino acids
    Uwe Wegner
    Falko Matthes
    Nicolaus von Wirén
    Ina Lemke
    Rüdiger Bode
    H.-Matthias Vorbrodt
    Marion Rauter
    Gotthard Kunze
    AMB Express, 13
  • [24] Dynamic Kinetic Resolution of α-Aminonitriles to Form Chiral α-Amino Acids
    Yasukawa, Kazuyuki
    Hasemi, Ryuji
    Asano, Yasuhisa
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (13) : 2328 - 2332
  • [25] Use of the Mitsunobu reaction in the synthesis of orthogonally protected α,β-diaminopropionic acids
    Kelleher, Fintan
    o Proinsias, Keith
    TETRAHEDRON LETTERS, 2007, 48 (28) : 4879 - 4882
  • [26] Synthesis of a homologous series of side-chain-extended orthogonally protected aminooxy-containing amino acids
    Liu, Fa
    Thomas, Joshua
    Burke, Terrence R., Jr.
    SYNTHESIS-STUTTGART, 2008, (15): : 2432 - 2438
  • [27] Stereoconservative synthesis of orthogonally protected gamma-functionalized amino acids using N-tritylserine derivatives
    Dugave, C
    Menez, A
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (17): : 6067 - 6070
  • [29] Asymmetric synthesis of α-amino acids via cinchona alkaloid-catalyzed kinetic resolution of urethane-protected α-amino acid N-carboxyanhydrides
    Hang, JF
    Tian, SK
    Tang, L
    Deng, L
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (50) : 12696 - 12697
  • [30] Synthesis of 4-Amino-Thiazole Analogs of Fmoc-Amino Acids and Thiazole Linked N-Orthogonally Protected Dipeptidomimetics
    Narendra, N.
    Vishwanatha, T. M.
    Sudarshan, N. S.
    Sureshbabu, Vommina V.
    PROTEIN AND PEPTIDE LETTERS, 2009, 16 (09): : 1029 - 1035