A rhodium-catalysed conjugate addition/cyclization cascade for the asymmetric synthesis of 2-amino-4H-chromenes

被引:8
|
作者
Chang, Zhiqian [1 ]
Zhu, Huilong [1 ]
Wu, Changhui [1 ]
Xing, Junhao [1 ]
Dou, Xiaowei [1 ]
机构
[1] China Pharmaceut Univ, Sch Sci, Dept Chem, Nanjing 211198, Peoples R China
基金
中国国家自然科学基金;
关键词
36;
D O I
10.1039/d0ob02404j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enantioselective synthesis of 2-amino-4H-chromenes via the cascade rhodium-catalysed conjugate addition/hetero Thorpe-Ziegler reaction is reported. Moderate to good yields (up to 98%) and high enantioselectivities (up to 92% ee) were obtained with a chiral diene-coordinated rhodium complex as the catalyst. This protocol remedies the methodological deficiency in the asymmetric synthesis of 4-aryl 2-amino-4H-chromenes.
引用
收藏
页码:785 / 788
页数:4
相关论文
共 50 条
  • [21] Synthesis of 2-amino-3-cyano-4H-chromen-4-ylphosphonates and 2-amino-4H-chromenes catalyzed by tetramethylguanidine
    Kalla, Reddi Mohan Naidu
    Byeon, Seong Jin
    Heo, Min Seon
    Kim, Il
    [J]. TETRAHEDRON, 2013, 69 (49) : 10544 - 10551
  • [22] Microwave Accelerated Synthesis of 2-Amino-4H-Chromenes Catalyzed by WELFSA: A Green Protocol
    Kantharaju, Kamanna
    Khatavi, Santosh Y.
    [J]. CHEMISTRYSELECT, 2018, 3 (18): : 5016 - 5024
  • [23] A multi-component electro-organic synthesis of 2-amino-4H-chromenes
    Makarem, S.
    Mohammadi, A. A.
    Fakhari, A. R.
    [J]. TETRAHEDRON LETTERS, 2008, 49 (50) : 7194 - 7196
  • [24] Effective and convenient synthesis of 2-amino-4H-chromenes promoted by melamine as a recyclable organocatalyst
    Kamali, Fatemeh
    Shirini, Farhad
    [J]. EURASIAN CHEMICAL COMMUNICATIONS, 2021, 3 (04): : 278 - 290
  • [25] Expeditious Synthesis of 2-Amino-4H-chromenes and 2-Amino-4H-pyran-3-carboxylates Promoted by Sodium Malonate
    Tazari, Mohsen
    Kiyani, Hamteh
    [J]. CURRENT ORGANIC SYNTHESIS, 2019, 16 (05) : 793 - 800
  • [26] Rhodium-catalysed enantioselective synthesis of 4-arylchroman-2-ones
    Allen, Joseph C.
    Kociok-Koehn, Gabriele
    Frost, Christopher G.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (01) : 32 - 35
  • [27] Highly efficient enantioselective three-component synthesis of 2-amino-4H-chromenes catalysed by chiral tertiary amine-thioureas
    Yang, Gaosheng
    Luo, Chongrong
    Mu, Xiaolong
    Wang, Tingting
    Liu, Xin-Yuan
    [J]. CHEMICAL COMMUNICATIONS, 2012, 48 (47) : 5880 - 5882
  • [28] Synthesis and characterization of functionalized nano NaY zeolite with metformin and use for the synthesis of 2-amino-4H-chromenes
    Niloofar Haghdadi
    Sakineh Asghari
    Ghasem Firouzzadeh Pasha
    [J]. Research on Chemical Intermediates, 2024, 50 : 1961 - 1992
  • [29] Synthesis and characterization of functionalized nano NaY zeolite with metformin and use for the synthesis of 2-amino-4H-chromenes
    Haghdadi, Niloofar
    Asghari, Sakineh
    Pasha, Ghasem Firouzzadeh
    [J]. RESEARCH ON CHEMICAL INTERMEDIATES, 2024, 50 (05) : 1961 - 1992
  • [30] MULTI-COMPONENT SYNTHESIS OF 2-AMINO-4H-CHROMENES CATALYZED BY NANO ZnO IN WATER
    Hosseini-Sarvari, Mona
    Shafiee-Haghighi, Sara
    [J]. COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2011, 76 (11) : 1285 - 1298