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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  • [51] (2S,3S)-Sulfated Pterosin C, a Cytotoxic Sesquiterpene from the Bangladeshi Mangrove Fern Acrostichum aureum
    Uddin, Shaikh J.
    Jason, Tracey L. H.
    Beattie, Karren D.
    Grice, I. Darren
    Tiralongo, Evelin
    [J]. JOURNAL OF NATURAL PRODUCTS, 2011, 74 (09): : 2010 - 2013
  • [52] Divergent NHC-Catalyzed Oxidative Transformations of 3-Bromoenal: Selective Synthesis of 2H-Pyran-2-ones and Chiral Dihydropyranones
    Wang, Gang
    Chen, Xia
    Miao, Gaohan
    Yao, Weijun
    Ma, Cheng
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (12) : 6223 - 6232
  • [53] Asymmetric Michael Addition of N-tert-Butanesulfinyl lmidate with α,β-Unsaturated Diesters: Scope and Application to the Synthesis of Indanone Derivatives
    Wang, Jinfang
    Zhou, Yu
    Zhang, Lei
    Li, Zeng
    Chen, Xianjie
    Liu, Hong
    [J]. ORGANIC LETTERS, 2013, 15 (07) : 1508 - 1511
  • [54] Catalytic Nazarov Reaction of Aryl Vinyl Ketones via Binary Acid Strategy
    Xi, Zhi-Guo
    Zhu, Lihui
    Luo, Sanzhong
    Cheng, Jin-Pei
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (02) : 606 - 613
  • [55] 2,3-heteroaromatic ring-fused cyclohexanones via heteroaromatic homo-Nazarov cyclization of donor-acceptor substituted cyclopropanes
    Yadav, Veejendra K.
    Kumar, Naganaboina Vijaya
    [J]. CHEMICAL COMMUNICATIONS, 2008, (32) : 3774 - 3776
  • [56] cis-2,3-Disubstituted Cyclopropane 1,1-Diesters in [3+2] Annulations with Aldehydes: Highly Diastereoselective Construction of Densely Substituted Tetrahydrofurans
    Yang, Gaosheng
    Sun, Yongxian
    Shen, Yue
    Chai, Zhuo
    Zhou, Shuangliu
    Chu, Jiang
    Chai, Jun
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (11) : 5393 - 5400
  • [57] AlCL3-Promoted Highly Regio- and Diastereoseletive [3+2] Cycloadditions of Activated Cyclopropanes and Aromatic Aldehydes: Construction of 2,5-Diaryl-3,3,4-trisubstituted Tetrahydrofurans
    Yang, Gaosheng
    Shen, Yue
    Li, Kui
    Sun, Yongxian
    Hua, Yuanyuan
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (01) : 229 - 233
  • [58] A Concise Synthesis of Paucifloral F and Related Indanone Analogues via Palladium-Catalyzed α-Arylation
    Yang, Yang
    Philips, Dean
    Pan, Shifeng
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (06) : 1902 - 1905
  • [59] Recent advances in donor-acceptor (DA) cyclopropanes
    Yu, M
    Pagenkopf, BL
    [J]. TETRAHEDRON, 2005, 61 (02) : 321 - 347
  • [60] Enantioselective Synthesis of Chiral 3-Aryl-1-indanones through Rhodium-Catalyzed Asymmetric Intramolecular 1,4-Addition
    Yu, Yue-Na
    Xu, Ming-Hua
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (06) : 2736 - 2741
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