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
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2021年 / 19卷 / 34期
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
  • [31] Kinetic Resolution of Oxazinones: Rational Exploration of Chemical Space through the Design of Experiments
    Renzi, Polyssena
    Kronig, Christel
    Carlone, Armando
    Eroksuz, Serap
    Berkessel, Albrecht
    Bella, Marco
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (37) : 11768 - 11775
  • [32] A Practical Aryl Unit for Azlactone Dynamic Kinetic Resolution: Orthogonally Protected Products and A Ligation-Inspired Coupling Process
    Tallon, Sean
    Manoni, Francesco
    Connon, Stephen J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (03) : 813 - 817
  • [33] Efficient Tandem Biocatalytic Process for the Kinetic Resolution of Aromatic β-Amino Acids
    Wu, Bian
    Szymanski, Wiktor
    de Wildeman, Stefaan
    Poelarends, Gerrit J.
    Feringa, Ben L.
    Janssen, Dick B.
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (09) : 1409 - 1412
  • [34] Controlled synthesis of chiral polymers for the kinetic resolution of racemic amino acids
    Li, Na
    Wang, Heng
    Zhang, Jie
    Wan, Xinhua
    POLYMER CHEMISTRY, 2014, 5 (05) : 1702 - 1710
  • [35] Kinetic resolution of urethane-protected α-amino acid n-carboxy anhydrides (UNCA) catalyzed by cinchona alkaloids:: Asymmetric synthesis of α-amino acids.
    Hang, JF
    Tian, SK
    Tang, L
    Deng, L
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U249 - U249
  • [36] Kinetic Resolution of 5-Substituted Oxazinones with Bifunctional Chiral Base/Squaramide Organocatalysts
    Eroeksuez, Serap
    Neudoerfl, Joerg M.
    Berkessel, Albrecht
    SYNLETT, 2017, 28 (11) : 1278 - 1281
  • [37] Orthogonally protected sugar diamino acids as building blocks for oligosaccharide mimetics
    Sicherl, Frank
    Wittmann, Valentin
    PEPTIDE REVOLUTION: GENOMICS, PROTEOMICS & THERAPEUTICS, 2004, : 161 - 162
  • [38] Stereoselective Synthesis of Orthogonally Protected β-Hydroxy-α-,γ-diamino Butyric Acids
    Stepan, Antonia F.
    Thuy-Trinh Nguyen
    Anderson, Dennis
    Liang, Huang
    Qian Zhanshan
    Magee, Thomas V.
    SYNLETT, 2011, (17) : 2499 - 2504
  • [39] Orthogonally Protected Thiazole and Isoxazole Diamino Acids: An Efficient Synthetic Route
    Butler, Jeffrey D.
    Coffman, Keith C.
    Ziebart, Kristin T.
    Toney, Michael D.
    Kurth, Mark J.
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (30) : 9002 - 9005
  • [40] Synthesis of orthogonally protected enantiopure 2,9-diaminodecanedioic acid:: A model for a new general method for the synthesis of orthogonally protected α,α′-diaminodicarboxylic acids
    Truchot, C
    Sasaki, NA
    HETEROCYCLES, 2004, 64 : 393 - 406
12345