Efficient organocatalytic asymmetric synthesis of 2-amino-4H-chromene-3-carbonitrile derivatives

被引：85
作者：
Gao, Yu [1 ]
Yang, Wen [1 ]
Du, Da-Ming [1 ]
机构：
[1] Beijing Inst Technol, Sch Chem Engn & Environm, Beijing 100081, Peoples R China
来源：
TETRAHEDRON-ASYMMETRY | 2012年 / 23卷 / 05期
基金：
中国国家自然科学基金;
关键词：
ENANTIOSELECTIVE MICHAEL ADDITION; HYDROGEN-BONDING DONORS; ONE-POT SYNTHESIS; HIGHLY EFFICIENT; AQUEOUS-MEDIA; BIFUNCTIONAL ORGANOCATALYSTS; CONJUGATE ADDITION; CHIRAL SQUARAMIDES; NITROALKENES; THIOUREA;
D O I：
10.1016/j.tetasy.2012.02.019
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The organocatalytic enantioselective tandem Michael addition-cyclization of malononitrile to nitroalkenes for the direct synthesis of chiral 2-amino-4H-chromene-3-carbonitrile derivatives was investigated. Good yields and enantioselectivities (up to 91% ee) were achieved. This organocatalytic asymmetric tandem Michael addition-cyclization provides an efficient route toward the synthesis of optically active functionalized chromenes. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：339 / 344
页数：6
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  • [1] Novel and efficient catalysts for the one-pot synthesis of 3,4-dihydropyrano[c]chromene derivatives in aqueous media
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    Balalaie, Saeed
    [J]. TETRAHEDRON LETTERS, 2007, 48 (18) : 3299 - 3303
  • [2] Squaramides: Bridging from Molecular Recognition to Bifunctional Organocatalysis
    Aleman, Jose
    Parra, Alejandro
    Jiang, Hao
    Jorgensen, Karl Anker
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (25) : 6890 - 6899
  • [3] Three-component process for the synthesis of 2-amino-2-chromenes in aqueous media
    Ballini, R
    Bosica, G
    Conforti, ML
    Maggi, R
    Mazzacani, A
    Righi, P
    Sartori, G
    [J]. TETRAHEDRON, 2001, 57 (07) : 1395 - 1398
  • [4] Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
  • [5] Efficient atom economical one-pot multicomponent synthesis of densely functionalized 4H-chromene derivatives
    Boominathan, Muthusamy
    Nagaraj, Muthupandi
    Muthusubramanian, Shanmugam
    Krishnakumar, Rajaputi Venkatraman
    [J]. TETRAHEDRON, 2011, 67 (33) : 6057 - 6064
  • [6] Pyrrolidine-thiourea as a bifunctional organocatalyst: Highly enantioselective Michael addition of cyclohexanone to nitroolefins
    Cao, Chun-Li
    Ye, Meng-Chun
    Sun, Xiu-Li
    Tang, Yong
    [J]. ORGANIC LETTERS, 2006, 8 (14) : 2901 - 2904
  • [7] Enantioselective One-Pot Synthesis of 2-Amino-4-(indol-3-yl)-4H-Chromenes
    Chen, Weiliang
    Cai, Yunfei
    Fu, Xuan
    Liu, Xiaohua
    Lin, Lili
    Feng, Xiaoming
    [J]. ORGANIC LETTERS, 2011, 13 (18) : 4910 - 4913
  • [8] Organocatalysis mediated by (thio)urea derivatives
    Connon, Stephen J.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (21) : 5418 - 5427
  • [9] A Bifunctional Cinchona Alkaloid-Squaramide Catalyst for the Highly Enantioselective Conjugate Addition of Thiols to trans-Chalcones
    Dai, Le
    Wang, Su-Xi
    Chen, Fen-Er
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (13) : 2137 - 2141
  • [10] Dalko P.I., 2007, ENANTIOSELECTIVE ORG
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