Organocatalytic Asymmetric One-Pot Sequential Conjugate Addition/Dearomative Fluorination: Synthesis of Chiral Fluorinated Isoxazol-5(4H)-ones

被引：52
|
作者：
Meng, Wen-Ting [1 ]
Zheng, Yan [1 ]
Nie, Jing [1 ]
Xiong, Heng-Ying [1 ]
Ma, Jun-An [1 ]
机构：
[1] Tianjin Univ, Dept Chem, Tianjin 300072, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 02期
基金：
中国国家自然科学基金;
关键词：
ENANTIOSELECTIVE MICHAEL ADDITION; STEREOSELECTIVE-SYNTHESIS; OXIDATIVE DEAROMATIZATION; FLAVANONE DERIVATIVES; MEDICINAL CHEMISTRY; FLUOROCYCLIZATION; TRANSFORMATION; CYCLIZATION; STRATEGIES; KETONES;
D O I：
10.1021/jo302419e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A facile one-pot sequential conjugate addition/dearomative fluorination transformation of isoxazol-5(4H)ones with nitroolefins and N-fluorobenzenesulfonimide (NFSI) has been developed. By using a bifunctional chiral tertiary amino-thiourea catalyst, a series of chiral fluorinated isoxazol-S(4H)-ones containing one fluorine-substituted quarternary stereocenter were obtained in high yields with high enantio- and diastereoselectivities. Further transformation of adducts could afford isoxazolidin-5-one derivatives with three contiguous stereocenters.
引用
收藏
页码：559 / 567
页数：9
相关论文
共 50 条
  • [1] One-pot synthesis of 3-methyl-4-arylmethylene-isoxazol-5(4H)-ones
    Zhang, Ying-Qun
    Ma, Jing-Jun
    Wang, Chun
    Li, Jing-Ci
    Zhang, Dong-Nuan
    Zang, Xiao-Huan
    Li, Jie
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2008, 28 (01) : 141 - 144
  • [2] One-pot and Three-Component Synthesis of Isoxazol-5 (4H)-one Derivatives in the presence of Citric Acid
    Rikani, Ashkan Bashash
    Setamdideh, Davood
    ORIENTAL JOURNAL OF CHEMISTRY, 2016, 32 (03) : 1433 - 1437
  • [3] Organocatalytic enantioselective Mannich reaction of isoxazol-5(4H)-ones to isatin-derived ketimines
    Toran, Ricardo
    Puchan, Dario
    Sanz-Marco, Amparo
    Vila, Carlos
    Pedro, Jose R.
    Blay, Gonzalo
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (43) : 8395 - 8399
  • [4] Facile Heterocyclic Synthesis and Antibacterial Activity of Substituted Isoxazol-5(4H)-ones
    Ferouani, Ghaniya
    Nacer, Amina
    Ameur, Nawal
    Bachir, Redouane
    Ziani-Cherif, Chewki
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2018, 65 (04) : 459 - 464
  • [5] One-pot green synthesis of isoxazol-5(4H)-one derivatives using Dowex1-x8OH in water
    Setamdideh, Davood
    JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 2016, 81 (09) : 971 - 978
  • [6] Facile and expedient synthesis of α,β-unsaturated isoxazol-5(4H)-ones under mild conditions
    Ghorbani, Fatemeh
    Kiyani, Hamzeh
    Pourmousavi, Seied Ali
    RESEARCH ON CHEMICAL INTERMEDIATES, 2020, 46 (01) : 943 - 959
  • [7] Facile and expedient synthesis of α,β-unsaturated isoxazol-5(4H)-ones under mild conditions
    Fatemeh Ghorbani
    Hamzeh Kiyani
    Seied Ali Pourmousavi
    Research on Chemical Intermediates, 2020, 46 : 943 - 959
  • [8] Magnetic nanoparticle supported choline chloride-glucose (deep eutectic solvent) for the one-pot synthesis of 3,4-disubstituted isoxazol-5(4H)-ones
    Hengameh Atharifar
    Ali Keivanloo
    Behrooz Maleki
    Mehdi Baghayeri
    Heshmatollah Alinezhad
    Research on Chemical Intermediates, 2024, 50 (1) : 281 - 296
  • [9] Magnetic nanoparticle supported choline chloride-glucose (deep eutectic solvent) for the one-pot synthesis of 3,4-disubstituted isoxazol-5(4H)-ones
    Atharifar, Hengameh
    Keivanloo, Ali
    Maleki, Behrooz
    Baghayeri, Mehdi
    Alinezhad, Heshmatollah
    RESEARCH ON CHEMICAL INTERMEDIATES, 2024, 50 (01) : 281 - 296
  • [10] Organocatalytic One-Pot Asymmetric Synthesis of 4H,5H-Pyrano[2,3-c]pyrazoles
    Enders, Dieter
    Grossmann, Andre
    Gieraths, Bianca
    Duezdemir, Muharrem
    Merkens, Carina
    ORGANIC LETTERS, 2012, 14 (16) : 4254 - 4257
12345