Lewis Acid-Mediated Transformations of trans-2-Aroyl-3-arylcyclopropane-1,1-dicarboxylates into 2-Pyrones and 1-Indanones

被引：31
作者：
Sathishkannan, Gopal [1 ]
Srinivasan, Kannupal [1 ]
机构：
[1] Bharathidasan Univ, Sch Chem, Tiruchirappalli 620024, Tamil Nadu, India
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 04期
关键词：
carbocycles; heterocycles; ring expansion; small ring systems; synthetic methods; DONOR-ACCEPTOR CYCLOPROPANES; NAZAROV CYCLIZATION; ALPHA-PYRONE; STEREOSELECTIVE-SYNTHESIS; MICHAEL ADDITION; DERIVATIVES; KETONES; INDANONES; ALDEHYDES; SCOPE;
D O I：
10.1002/adsc.201300861
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
trans-2-Aroyl-3-arylcyclopropane-1,1-dicarboxylates upon treatment with aluminium(III) chloride (AlCl3) underwent ring-opening, fragmentation, recombination and lactonization to give highly substituted 2-pyrones. Alternatively, when treated with titanium(IV) chloride (TiCl4), the cyclopropane diesters underwent a Nazarov cyclization to afford 1-indanones with high diastereoselectivity.
引用
收藏
页码：729 / 735
页数：7
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共 61 条
  • [1] Indene-based scaffolds. Design and synthesis of novel serotonin 5-HT6 receptor ligands[J]. Alcalde, Ermitas;Mesquida, Neus;Frigola, Jordi;Lopez-Perez, Sara;Merce, Ramon. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008(20)
  • [2] [Anonymous], 2010, ANGEW CHEM
  • [3] Stereoselective synthesis of 3-aminoindan-1-ones and subsequent incorporation into HIV-1 protease inhibitors[J]. Arefalk, A;Wannberg, J;Larhed, M;Hallberg, A. JOURNAL OF ORGANIC CHEMISTRY, 2006(03)
  • [4] Heterocycles from cyclopropanes: applications in natural product synthesis[J]. Carson, Cheryl A.;Kerr, Michael A. CHEMICAL SOCIETY REVIEWS, 2009(11)
  • [5] Chaladaj W., 2012, ANGEW CHEM, V124, P7035
  • [6] Total Synthesis of Neurymenolide A Based on a Gold-Catalyzed Synthesis of 4-Hydroxy-2-pyrones[J]. Chaladaj, Wojciech;Corbet, Matthieu;Fuerstner, Alois. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012(28)
  • [7] Catalytic Selective Cyclizations of Aminocyclopropanes: Formal Synthesis of Aspidospermidine and Total Synthesis of Goniomitine[J]. De Simone, Filippo;Gertsch, Juerg;Waser, Jerome. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010(33)
  • [8] Cyclization and Cycloaddition Reactions of Cyclopropyl Carbonyls and Imines[J]. De Simone, Filippo;Waser, Jerome. SYNTHESIS-STUTTGART, 2009(20)
  • [9] Catalytic Formal Homo-Nazarov Cyclization[J]. De Simone, Filippo;Andres, Julien;Torosantucci, Riccardo;Waser, Jerome. ORGANIC LETTERS, 2009(04)
  • [10] MICROBIAL PYRAN-2-ONES AND DIHYDROPYRAN-2-ONES[J]. DICKINSON, JM. NATURAL PRODUCT REPORTS, 1993(01)
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