Stereoselective Multicomponent Reactions in the Synthesis or Transformations of Epoxides and Aziridines

被引:25
|
作者
da Silva, Allan Ribeiro [1 ]
dos Santos, Deborah Araujo [1 ,2 ]
Paixao, Marcio Weber [1 ]
Correa, Arlene Goncalves [1 ]
机构
[1] Univ Fed Sao Carlos, Ctr Excellence Res Sustainable Chem, Dept Chem, BR-13565905 Sao Carlos, SP, Brazil
[2] Univ Sao Paulo, Sao Carlos Inst Chem, BR-13563120 Sao Carlos, SP, Brazil
来源
MOLECULES | 2019年 / 24卷 / 03期
基金
巴西圣保罗研究基金会;
关键词
multicomponent reactions; epoxides; aziridine; asymmetric synthesis; green synthesis; RING-EXPANSION CASCADE; ONE-POT SYNTHESIS; BETA-AMINO ACID; STEREOSPECIFIC SYNTHESIS; ASYMMETRIC-SYNTHESIS; 3-COMPONENT REACTION; ALDEHYDE DIMERS; CARBON-MONOXIDE; N-H; CATALYSIS;
D O I
10.3390/molecules24030630
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Small ring heterocycles, such as epoxides and aziridines, are present in several natural products and are also highly versatile building blocks, frequently involved in the synthesis of numerous bioactive products and pharmaceuticals. Because of the potential for increased efficiency and selectivity, along with the advantages of environmentally benign synthetic procedures, multicomponent reactions (MCRs) have been explored in the synthesis and ring opening of these heterocyclic units. In this review, the recent advances in MCRs involving the synthesis and applications of epoxides and aziridines to the preparation of other heterocycles are discussed emphasizing the stereoselectivity of the reactions.
引用
收藏
页数:23
相关论文
共 50 条
  • [41] Stereoselective Divergent Synthesis of Chiral Pyrazolone Derivatives via Multicomponent Cascade Reactions by Isothiourea Catalysis
    Liu, Xin
    Chen, Siyi
    Huang, Jun
    Liang, Peiyao
    Zhou, Liejin
    Wang, Shoulei
    ORGANIC LETTERS, 2024, 27 (01) : 433 - 438
  • [42] Highly Stereoselective Synthesis of Substituted Prolyl Peptides Using a Combination of Biocatalytic Desymmetrization and Multicomponent Reactions
    Znabet, Anass
    Ruijter, Eelco
    de Kanter, Frans J. J.
    Koehler, Valentin
    Helliwell, Madeleine
    Turner, Nicholas J.
    Orru, Romano V. A.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (31) : 5289 - 5292
  • [43] Organocatalyzed enantioselective desymmetrization of aziridines and epoxides
    Wang, Ping-An
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 : 1677 - 1695
  • [44] Completely Stereoselective Synthesis of Sulfonated 1,3-Dihydroisobenzofurans via Radical Multicomponent Reactions
    Shi, Hao-Nan
    Huang, Min-Hua
    He, Chun-Lan
    Lu, Hai-Ping
    Hao, Wen-Juan
    Tu, Xing-Chao
    Tu, Shu-Jiang
    Jiang, Bo
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (21): : 13686 - 13695
  • [45] Photochemical Synthesis and Ring-Opening of Aziridines and Epoxides: State-of-the-Art
    Furniel, Lucas G.
    Correa, Arlene G.
    CHEMPHOTOCHEM, 2024, 8 (09):
  • [46] Two-step synthesis of N-sulfonyl aziridines from epoxides
    Huang, Jianhui
    O'Brien, Peter
    Synthesis, 2006, (03) : 425 - 434
  • [47] Two-step synthesis of N-sulfonyl aziridines from epoxides
    Huang, JH
    O'Brien, P
    SYNTHESIS-STUTTGART, 2006, (03): : 425 - 434
  • [48] A NOVEL CATALYTIC CYCLE FOR THE SYNTHESIS OF EPOXIDES USING SULFUR YLIDES, AND APPLICATION TO THE SYNTHESIS OF CYCLOPROPANES AND AZIRIDINES
    AGGARWAL, VK
    ABDELRAHMAN, H
    THOMPSON, A
    MATTISON, B
    JONES, RVH
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1994, 95-6 (1-4): : 283 - 292
  • [49] Mild metal-free syn-stereoselective ring opening of activated epoxides and aziridines with aryl borates
    Pineschi, M
    Bertolini, F
    Haak, RM
    Crotti, P
    Macchia, F
    CHEMICAL COMMUNICATIONS, 2005, (11) : 1426 - 1428
  • [50] On the utility of S-mesitylsulfinimines for the stereoselective synthesis of chiral amines and aziridines
    Roe, Caroline
    Sola, Toni Moragas
    Sasraku-Neequaye, Leonid
    Hobbs, Heather
    Churcher, Ian
    MacPherson, David
    Stockman, Robert A.
    CHEMICAL COMMUNICATIONS, 2011, 47 (26) : 7491 - 7493