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Stannylcupration of Acetylenes Followed by Reaction with Epoxides:  A Novel Annulation Strategy for the Synthesis of Cyclobutenes

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    Stannylcupration of Acetylenes Followed by Reaction with Epoxides:  A Novel Annulation Strategy for the Synthesis of Cyclobutenes
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    Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, Valladolid 47011, Spain
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 1998, 63, 21, 7531–7533
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo980874s
    Published September 24, 1998
    Copyright © 1998 American Chemical Society
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    Copyright © 1998 American Chemical Society

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    Full spectroscopic and analytical data for compound 6b. Experimental procedure for the tosylation of alcohols 3 and 6, as well as 1H NMR characterization data of all tosylates (1 page). This material is contained in libraries on microfiche, immediately follows this article in the microfilm version of the journal, and can be ordered from the ACS; see any current masthead page for ordering information.

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    Cited By

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    This article is cited by 34 publications.

    1. Alberto Brandi, Stefano Cicchi, Franca M. Cordero, and Andrea Goti . Progress in the Synthesis and Transformations of Alkylidenecyclopropanes and Alkylidenecyclobutanes. Chemical Reviews 2014, 114 (15) , 7317-7420. https://doi.org/10.1021/cr400686j
    2. Xiaoyi Xin, Dongping Wang, Fan Wu, Chunxiang Wang, Haolong Wang, Xincheng Li, and Boshun Wan . Synthesis of Polyfluoroalkyl Cyclobutenes from 3-Aza-1,5-enynes via an Aza-Claisen Rearrangement/Cyclization Cascade. Organic Letters 2013, 15 (17) , 4512-4515. https://doi.org/10.1021/ol4020738
    3. J. R. Falck, Anish Bandyopadhyay, Narender Puli, Abhijit Kundu, L. Manmohan Reddy, Deb K. Barma, Anyu He, Hongming Zhang, Dhurke Kashinath and Rachid Baati. Cascade Synthesis of (E)-2-Alkylidenecyclobutanols. Organic Letters 2009, 11 (20) , 4764-4766. https://doi.org/10.1021/ol901985c
    4. Helen M. Sheldrake,, Timothy W. Wallace, and, Craig P. Wilson. Functionalized Cyclobutenes via Multicomponent Thermal [2 + 2] Cycloaddition Reactions. Organic Letters 2005, 7 (19) , 4233-4236. https://doi.org/10.1021/ol051675f
    5. Shengming Ma. Some Typical Advances in the Synthetic Applications of Allenes. Chemical Reviews 2005, 105 (7) , 2829-2872. https://doi.org/10.1021/cr020024j
    6. Asunción Barbero,, Francisco J. Pulido, and, Juan A. Rincón. Addition of Organometallic Compounds to Tin-Containing Cyclic Ketones. Remote Stereocontrol Induced by the Stannyl Group. Journal of the American Chemical Society 2003, 125 (39) , 12049-12056. https://doi.org/10.1021/ja036340c
    7. A. A. A. Al Quntar, H. Dweik, V. Dembitsky. Facile Synthesis of 2-Aminocyclobutenylphosphonates. Russian Journal of Organic Chemistry 2020, 56 (1) , 137-142. https://doi.org/10.1134/S1070428020010212
    8. Richard C. Larock, Anton V. Dubrovskiy, Nataliya A. Markina. Formation of Alkenes by Cyclization, Annulation, and Related Reactions. 2018, 1-37. https://doi.org/10.1002/9781118662083.cot02-009
    9. Tse‐Lok Ho. Organocopper reagents. 2017https://doi.org/10.1002/9780471264194.fos07464.pub5
    10. Tse‐Lok Ho, Mary Fieser, Rick Danheiser, William Roush, Janice Smith, Louis Fieser. Organocopper reagents. 2017https://doi.org/10.1002/9780471264194.fos07464.pub6
    11. Tse‐Lok Ho, Mary Fieser, Rick Danheiser, William Roush, Janice Smith, Louis Fieser. Organocopper Reagents. 2013, 321-322. https://doi.org/10.1002/9780471264194.fos07464.pub4
    12. Masashi Ishigaki, Mio Inumaru, Tsuyoshi Satoh. New synthesis of allylidenecyclobutanes by the reaction of cyclobutylmagnesium carbenoids with vinyl sulfones. Tetrahedron Letters 2011, 52 (43) , 5563-5566. https://doi.org/10.1016/j.tetlet.2011.08.018
    13. Tse‐Lok Ho, Mary Fieser, Rick Danheiser, William Roush, Janice Smith, Louis Fieser. Organocopper Reagents. 2011, 385-386. https://doi.org/10.1002/9780471264194.fos07464.pub3
    14. Francisco J. Pulido, Asunción Barbero. Silyl and Stannyl Derivatives of Organocopper Compounds. 2011https://doi.org/10.1002/9780470682531.pat0449
    15. Hemant K. Sharma, Ionel Haiduc, Keith H. Pannell. Transition Metal Complexes of Germanium, Tin and Lead. 2009https://doi.org/10.1002/9780470682531.pat0269
    16. Eric Fouquet. Synthetic Applications of Organic Germanium, Tin and Lead Compounds (Excluding R 3 MH ). 2009https://doi.org/10.1002/9780470682531.pat0270
    17. E. Lee‐Ruff. Synthesis of Cyclobutanes. 2009https://doi.org/10.1002/9780470682531.pat0322
    18. Tse‐Lok Ho, Mary Fieser, Rick Danheiser, William Roush, Janice Smith, Louis Fieser. Organocopper reagents. 2009, 000-000. https://doi.org/10.1002/9780471264194.fos07464.pub2
    19. Yulia Sinelnikove, Abraham Rubinstein, Morris Srebnik, Abed Al Aziz Al Quntar. Direct formation of cyclobutenylphosphonates from 1-alkynylphosphonates and Cp2ZrCl2/2EtMgCl/2CuCl. Tetrahedron Letters 2009, 50 (8) , 867-869. https://doi.org/10.1016/j.tetlet.2008.11.108
    20. G. Dake. Oxiranes and Oxirenes: Monocyclic. 2008, 173-233. https://doi.org/10.1016/B978-008044992-0.00103-6
    21. Michael T. Crimmins, Francisco J. Pulido, Pilar Castreño, Asunción Barbero. Allene. 2007https://doi.org/10.1002/9780470842898.ra038.pub2
    22. A. Baba, I. Shibata, M. Yasuda. Tin. 2007, 341-379. https://doi.org/10.1016/B0-08-045047-4/00115-1
    23. Asunción Barbero, Francisco J Pulido, M Carmen Sañudo. Allylsilanes in the synthesis of three to seven membered rings: the silylcuprate strategy. Beilstein Journal of Organic Chemistry 2007, 3 https://doi.org/10.1186/1860-5397-3-16
    24. Tse‐Lok Ho, Mary Fieser, Rick Danheiser, William Roush, Janice Smith, Louis Fieser. Organocopper reagents. 2006https://doi.org/10.1002/9780471264194.fos07464
    25. Jean‐Mathieu Chrétien, Françoise Zammattio, Delphine Gauthier, Erwan Le Grognec, Michaël Paris, Jean‐Paul Quintard. Preparation of Allyltin Reagents Grafted on Solid Support: Clean and Easily Recyclable Reagents for Allylation of Aldehydes. Chemistry – A European Journal 2006, 12 (26) , 6816-6828. https://doi.org/10.1002/chem.200501595
    26. Steven H. Bertz, Edward H. Fairchild, Karl Dieter. Copper(I) Cyanide. 2006https://doi.org/10.1002/047084289X.rc224.pub2
    27. Asunción Barbero, Francisco J. Pulido. Allylstannanes and vinylstannanes from stannylcupration of C–C multiple bonds. Recent advances and applications in organic synthesis. Chemical Society Reviews 2005, 34 (11) , 913. https://doi.org/10.1039/b506622k
    28. Asunción Barbero, Francisco J. Pulido. The regiochemistry of the stannylcupration of allenes: synthesis of allylstannanes using the lower order cuprate (Bu3Sn)CuCNLi. Tetrahedron Letters 2004, 45 (19) , 3765-3767. https://doi.org/10.1016/j.tetlet.2004.03.079
    29. Morshed Alam Chowdhury, Hisanori Senboku, Masao Tokuda. A new synthesis of ring-fused alkylidenecyclobutanes by ring-enlargement reaction of bicyclo[n.1.0]alkylidene derivatives. Tetrahedron Letters 2003, 44 (16) , 3329-3332. https://doi.org/10.1016/S0040-4039(03)00571-9
    30. Asunción Barbero, Francisco J. Pulido, Juan A. Rincón, Purificación Cuadrado, Diego Galisteo, Henar Martínez-García. Remote Stereocontrol in Carbonyl Additions Promoted by Vinylstannanes. Angewandte Chemie 2001, 113 (11) , 2159-2161. https://doi.org/10.1002/1521-3757(20010601)113:11<2159::AID-ANGE2159>3.0.CO;2-8
    31. Asunción Barbero, Francisco J. Pulido, Juan A. Rincón, Purificación Cuadrado, Diego Galisteo, Henar Martínez-García. Remote Stereocontrol in Carbonyl Additions Promoted by Vinylstannanes. Angewandte Chemie International Edition 2001, 40 (11) , 2101-2103. https://doi.org/10.1002/1521-3773(20010601)40:11<2101::AID-ANIE2101>3.0.CO;2-H
    32. Jing Feng, Günter Szeimies. An Efficient Synthesis of Arylcyclobutenes via Cross-Coupling of Aryl Halides with 1-(Tri- n -butylstannyl)cyclobutene. Tetrahedron 2000, 56 (25) , 4249-4252. https://doi.org/10.1016/S0040-4020(00)00350-1
    33. Asunción Barbero, Carlos García, Francisco J. Pulido. Silylcupration of allenes followed by reaction with enones. A new strategy for the synthesis of methylenecyclopentanols. Tetrahedron Letters 1999, 40 (36) , 6649-6652. https://doi.org/10.1016/S0040-4039(99)01264-2
    34. Asuncion Barbero, Purificacion Cuadrado, Carlos Garcia, Juan A. Rincon, Francisco J. Pulido. ChemInform Abstract: Stannylcupration of Acetylenes Followed by Reaction with Epoxides: A Novel Annulation Strategy for the Synthesis of Cyclobutenes.. ChemInform 1999, 30 (13) https://doi.org/10.1002/chin.199913103
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 1998, 63, 21, 7531–7533
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo980874s
    Published September 24, 1998
    Copyright © 1998 American Chemical Society
    Request reuse permissions

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