Enantioselective synthesis of 4-hydroxy-D-pyroglutamic acid derivatives by an asymmetric 1,3-dipolar cycloaddition

被引：36
|
作者：
Merino, P [1 ]
Revuelta, J
Tejero, T
Chiacchio, U
Rescifina, A
Piperno, A
Romeo, G
机构：
[1] Univ Zaragoza, Fac Ciencias, ICMA, Dept Quim Organ, E-50009 Zaragoza, Spain
[2] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy
[3] Univ Messina, Dipartimento Farmacochim, I-98168 Messina, Italy
来源：
TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 02期
关键词：
D O I：
10.1016/S0957-4166(02)00072-1
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The 1,3-dipolar cycloaddition of a chiral nitrone derived from glyoxylic acid and protected D-ribosyl hydroxylamine with the acrylamide of Oppolzer's sultam provides a perfectly stereoselective approach to protected (2R,4R)-4-hydroxy-D-pyro-lutamic acid. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：167 / 172
页数：6
相关论文
共 50 条
  • [1] ENANTIOSELECTIVE TOTAL SYNTHESIS OF (+)-NEGAMYCIN AND (-)-EPINEGAMYCIN BY AN ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION
    IIDA, H
    KASAHARA, K
    KIBAYASHI, C
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (15) : 4647 - 4648
  • [2] Synthesis of spirooxindoles via asymmetric 1,3-dipolar cycloaddition
    Ding, K
    Wang, GP
    Deschamps, JR
    Parrish, DA
    Wang, SM
    TETRAHEDRON LETTERS, 2005, 46 (35) : 5949 - 5951
  • [3] Experimental and theoretical study of the 1,3-dipolar cycloaddition between D-glyceraldehyde nitrones and acrylates. Diastereoselective approach to 4-hydroxy pyroglutamic acid derivatives
    Merino, P
    Mates, JA
    Revuelta, J
    Tejero, T
    Chiacchio, U
    Romeo, G
    Iannazzo, D
    Romeo, R
    TETRAHEDRON-ASYMMETRY, 2002, 13 (02) : 173 - 190
  • [4] Asymmetric 1,3-dipolar cycloaddition reactions
    Center for Metal Catalyzed Reactions, Department of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark
    不详
    不详
    不详
    不详
    不详
    Chem. Rev., 2 (863-909):
  • [5] Asymmetric 1,3-dipolar cycloaddition reactions
    Gothelf, KV
    Jorgensen, KA
    CHEMICAL REVIEWS, 1998, 98 (02) : 863 - 909
  • [6] AN ENANTIOSELECTIVE SYNTHESIS OF (+)-CROTANECINE BY AN INTRAMOLECULAR AZIDE 1,3-DIPOLAR CYCLOADDITION
    BENNETT, RB
    CHA, JK
    TETRAHEDRON LETTERS, 1990, 31 (38) : 5437 - 5440
  • [7] Enantioselective synthesis of proline derivatives by 1,3-dipolar cycloadditions
    Najera, Carmen
    Sansano, Jose M.
    MONATSHEFTE FUR CHEMIE, 2011, 142 (07): : 659 - 680
  • [8] Enantioselective synthesis of proline derivatives by 1,3-dipolar cycloadditions
    Carmen Nájera
    José M. Sansano
    Monatshefte für Chemie - Chemical Monthly, 2011, 142 : 659 - 680
  • [9] Diastereo- and Enantioselective Synthesis of Fluorinated Proline Derivatives via Copper(I)-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition
    Li, Qing
    Ding, Chang-Hua
    Li, Xiao-Hui
    Weissensteiner, Walter
    Hou, Xue-Long
    SYNTHESIS-STUTTGART, 2012, 44 (02): : 265 - 271
  • [10] Silver/Segphos-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition for the Enantioselective Synthesis of Pyrrolidine Spirooxindoles
    Ma, Yangmin
    Dang, Gege
    Qi, Simeng
    Zhang, Xuemei
    Sun, Zhaoyang
    Miao, Xia
    Ma, Siyue
    Zhou, Haojie
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (45)
12345