MiPNO, a new chiral cyclic nitrone for enantioselective amino acid synthesis the cycloaddition approach

被引：23
|
作者：
Thiverny, Maryse [1 ]
Philouze, Christian [1 ]
Chavant, Pierre Yves [1 ]
Blandin, Veronique [1 ]
机构：
[1] Univ Grenoble 1, CNRS, ICMG FR 2607, Dept Chim Mol,UMR 5250, F-38041 Grenoble, France
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 04期
关键词：
1,3-DIPOLAR CYCLOADDITION; ALPHA-ALKOXYCARBONYLNITRONES; BUILDING-BLOCKS; N-HYDROXY; ACCESS; REARRANGEMENT; PRECURSORS; PRINCIPLE; PEPTIDES; REAGENTS;
D O I：
10.1039/b918612c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The resolution of chiral nitrones via derivatization of hydroxylamines was applied to MiPNO, a new, stable, easily prepared chiral cyclic nitrone. The application of MiPNO in totally regio- and diastereo-selective 1,3-dipolar cycloaddition reactions provides an expeditious enantioselective access to unusual gamma-hydroxy alpha-amino acids.
引用
收藏
页码：864 / 872
页数：9
相关论文
共 50 条
  • [41] A Chiral COFs Membrane for Enantioselective Amino Acid Separation
    Manoranjan, Narmadha
    Fang, Wangxi
    Zhu, Yuzhang
    Jin, Jian
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (05)
  • [42] New enantioselective approach to the total synthesis of (-)-α-kainic acid
    Rubio, A
    Ezquerra, J
    Escribano, A
    Remuiñán, MJ
    Vaquero, JJ
    TETRAHEDRON LETTERS, 1998, 39 (15) : 2171 - 2174
  • [43] Enantioselective hydrolysis of α-amino acid ester by chiral metallomicelles
    You, JS
    Yu, XQ
    Zhang, XL
    Xie, RG
    CHINESE CHEMICAL LETTERS, 1998, 9 (04) : 335 - 337
  • [44] Chiral Phosphoric Acid Catalyzed Enantioselective Synthesis of β-Amino-α, α-difluoro Carbonyl Compounds
    Kashikura, Wataru
    Mori, Keiji
    Akiyama, Takahiko
    ORGANIC LETTERS, 2011, 13 (07) : 1860 - 1863
  • [45] Chiral Bronsted acid catalyzed enantioselective hydrophosphonylation of imines:: Asymmetric synthesis of α-amino phosphonates
    Akiyama, T
    Morita, H
    Itoh, J
    Fuchibe, K
    ORGANIC LETTERS, 2005, 7 (13) : 2583 - 2585
  • [46] Novel chiral imidazole cyclophane receptors: synthesis and enantioselective recognition for amino acid derivatives
    You, JS
    Yu, XQ
    Zhang, GL
    Xiang, QX
    Lan, JB
    Xie, RG
    CHEMICAL COMMUNICATIONS, 2001, (18) : 1816 - 1817
  • [47] High throughput solid-phase screening of bacteria with cyclic amino alcohol deamination activity for enantioselective synthesis of chiral cyclic β-amino alcohols
    Ya-Wen Chang
    Jian-Dong Zhang
    Xiao-Xiao Yang
    Jing Li
    Li-Li Gao
    Shuang-Ping Huang
    Xing-Mei Guo
    Cao-Feng Zhang
    Hong-Hong Chang
    Jian-He Xu
    Biotechnology Letters, 2020, 42 : 1501 - 1511
  • [48] High throughput solid-phase screening of bacteria with cyclic amino alcohol deamination activity for enantioselective synthesis of chiral cyclic β-amino alcohols
    Chang, Ya-Wen
    Zhang, Jian-Dong
    Yang, Xiao-Xiao
    Li, Jing
    Gao, Li-Li
    Huang, Shuang-Ping
    Guo, Xing-Mei
    Zhang, Cao-Feng
    Chang, Hong-Hong
    Xu, Jian-He
    BIOTECHNOLOGY LETTERS, 2020, 42 (08) : 1501 - 1511
  • [49] Catalytic Enantioselective Synthesis of Chiral 3-Amino-2-oxindoles by a Mannich Approach
    Yanagisawa, Akira
    Kushihara, Naoyuki
    Sugita, Takuya
    Horiguchi, Moe
    Ida, Kazuki
    Yoshida, Kazuhiro
    SYNLETT, 2015, 26 (18) : 2541 - 2546
  • [50] NEW SYNTHESIS OF BETA-LACTAMS BASED ON NITRONE CYCLOADDITION TO NITROALKENES
    PADWA, A
    KOEHLER, KF
    RODRIGUEZ, A
    JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (02): : 282 - 288
12345