ACS Publications. Most Trusted. Most Cited. Most Read
Amine-Catalyzed Coupling of Aldehydes and Ketenes Derived from Fischer Carbene Complexes:  Formation of β-Lactones and Enol Ethers

OR SEARCH CITATIONS

My Activity
Publications

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Org. Chem. 2003, 68, 15, 6056-6059
    Note

    Amine-Catalyzed Coupling of Aldehydes and Ketenes Derived from Fischer Carbene Complexes:  Formation of β-Lactones and Enol Ethers
    Click to copy article linkArticle link copied!

    View Author Information
    Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles Young Drive, Los Angeles, California 90095-1569 %[email protected]
    Other Access OptionsSupporting Information (1)

    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2003, 68, 15, 6056–6059
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo034476n
    Published June 26, 2003
    Copyright © 2003 American Chemical Society
    Request reuse permissions

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    Aldehydes react with ketenes generated from photolysis of Fischer chromium carbene complexes to generate either β-lactones or enol ethers resulting from decarboxylation of β-lactones. The reaction is catalyzed by tertiary amines and can occur with diastereoselectivity greater than 20:1 with DMAP as the catalyst.

    Copyright © 2003 American Chemical Society

    Subjects

    what are subjects

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    *

     Corresponding author.

    Supporting Information Available

    Click to copy section linkSection link copied!

    Experimental procedures and spectral data for compounds 3b/b‘, 3c/c‘, 3d/d‘, 3e/e‘, 4g/g‘, 4h/h‘, 7a/b, and 8 and copies of 1H NMR spectra for compounds 3−5, 7, and 8. This material is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Electronic Supporting Information files are available without a subscription to ACS Web Editions. The American Chemical Society holds a copyright ownership interest in any copyrightable Supporting Information. Files available from the ACS website may be downloaded for personal use only. Users are not otherwise permitted to reproduce, republish, redistribute, or sell any Supporting Information from the ACS website, either in whole or in part, in either machine-readable form or any other form without permission from the American Chemical Society. For permission to reproduce, republish and redistribute this material, requesters must process their own requests via the RightsLink permission system. Information about how to use the RightsLink permission system can be found at http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!
    Citation Statements
    Explore this article's citation statements on scite.ai
    powered by  Scite

    This article is cited by 26 publications.

    1. Mukulesh Mondal, Shi Chen, Nabil Othman, Kraig A. Wheeler, and Nessan J. Kerrigan . Phosphine-Catalyzed Diastereoselective Synthesis of β-Lactones from Disubstituted Ketenes and α-Chiral Oxyaldehydes. The Journal of Organic Chemistry 2015, 80 (11) , 5789-5794. https://doi.org/10.1021/acs.joc.5b00869
    2. Cunxiang Zhao, T. Andrew Mitchell, Ravikrishna Vallakati, Lisa M. Pérez, and Daniel Romo . Mechanistic Investigations of the ZnCl2-Mediated Tandem Mukaiyama Aldol Lactonization: Evidence for Asynchronous, Concerted Transition States and Discovery of 2-Oxopyridyl Ketene Acetal Variants. Journal of the American Chemical Society 2012, 134 (6) , 3084-3094. https://doi.org/10.1021/ja209163w
    3. Henry Nguyen, Gil Ma, Tatiana Gladysheva, Trisha Fremgen, and Daniel Romo . Bioinspired Total Synthesis and Human Proteasome Inhibitory Activity of (−)-Salinosporamide A, (−)-Homosalinosporamide A, and Derivatives Obtained via Organonucleophile Promoted Bis-cyclizations. The Journal of Organic Chemistry 2011, 76 (1) , 2-12. https://doi.org/10.1021/jo101638r
    4. Hideaki Fujii, Satomi Imaide, Akio Watanabe, Kenji Yoza, Mayumi Nakajima, Kaoru Nakao, Hidenori Mochizuki, Noriko Sato, Toru Nemoto and Hiroshi Nagase . A Double Decarboxylation Reaction of an Oxazolidinone and Carboxylic Acid: Its Application to the Synthesis of a New Opioid Lead Compound. The Journal of Organic Chemistry 2010, 75 (3) , 995-998. https://doi.org/10.1021/jo9025463
    5. Mokhles M. Abd-Elzaher,, Bernhard Weibert, and, Helmut Fischer. Photoinduced Coupling of CO and Vinylidene LigandsFormation of Cyclobutane-1,3-diones. Organometallics 2005, 24 (6) , 1050-1052. https://doi.org/10.1021/om049188b
    6. José Barluenga,, Javier Santamaría, and, Miguel Tomás. Synthesis of Heterocycles via Group VI Fischer Carbene Complexes. Chemical Reviews 2004, 104 (5) , 2259-2284. https://doi.org/10.1021/cr0306079
    7. Navjeet Kaur. Synthesis of oxetanes from carbonyl compounds. 2023, 79-105. https://doi.org/10.1016/B978-0-443-18947-0.00004-3
    8. Navjeet Kaur. Synthesis of oxetanes under photochemical irradiation. 2023, 321-340. https://doi.org/10.1016/B978-0-443-18947-0.00008-0
    9. Tse‐Lok Ho, Mary Fieser, Janice Smith, Louis Fieser. Chromium – Carbene Complexes. 2017https://doi.org/10.1002/9780471264194.fos02739.pub6
    10. Lin Chen, Zhijun Wu, Lin Peng, Qilin Wang, Xiaoying Xu, Lixin Wang. A New Cyclization/Decarboxylation Reaction of Isatins with Acyl Chlorides for the Facile Synthesis of 3‐Alkenyl‐Oxindoles. Chinese Journal of Chemistry 2014, 32 (9) , 844-852. https://doi.org/10.1002/cjoc.201400320
    11. Morelia E. López-Reyes, José G. López-Cortés, M. Carmen Ortega-Alfaro, R. Alfredo Toscano, Cecilio Alvarez-Toledano. First direct synthesis of 3-hydroxy-pent-4-ynoic acids. Application to the synthesis of pyran-2-ones. Tetrahedron 2013, 69 (35) , 7365-7372. https://doi.org/10.1016/j.tet.2013.06.069
    12. Tse‐Lok Ho, Mary Fieser, Janice Smith, Louis Fieser. Chromium – Carbene Complexes. 2013, 207-208. https://doi.org/10.1002/9780471264194.fos02739.pub5
    13. Tse‐Lok Ho, Mary Fieser, Janice Smith, Louis Fieser. Chromium – Carbene Complexes. 2011, 207-208. https://doi.org/10.1002/9780471264194.fos02739.pub4
    14. Tse‐Lok Ho, Mary Fieser, Janice Smith, Louis Fieser. Chromium carbene complexes. 2010, 000-000. https://doi.org/10.1002/9780471264194.fos02739.pub3
    15. Hiroshi Nagase, Hideaki Fujii. Synthesis of Novel Basic Skeletons Derived from Naltrexone. 2010, 187-237. https://doi.org/10.1007/128_2010_75
    16. Tse‐Lok Ho, Mary Fieser, Janice Smith, Louis Fieser. Chromium carbene complexes. 2009, 000-000. https://doi.org/10.1002/9780471264194.fos02739.pub2
    17. Thomas M. Mitzel, Julie A. Pigza. Ketene. 2009https://doi.org/10.1002/047084289X.rk000.pub2
    18. Daniel Romo, Vikram C. Purohit, Andrea S. Matla. Recent Advances in Lewis Base-Catalyzed, Stereoselective Tandem Aldol b- and g-Lactonizations. HETEROCYCLES 2008, 76 (2) , 949. https://doi.org/10.3987/REV-08-SR(N)7
    19. Pedro J. Campos, Míriam Caro, Susana López-Sola, Diego Sampedro, Miguel A. Rodríguez. Role of imino group in photochemical reactions of Fischer carbene complexes. Journal of Organometallic Chemistry 2006, 691 (5) , 1075-1080. https://doi.org/10.1016/j.jorganchem.2005.11.025
    20. James W. Herndon. The chemistry of the carbon-transition metal double and triple bond: annual survey covering the year 2003. Coordination Chemistry Reviews 2005, 249 (9-10) , 999-1083. https://doi.org/10.1016/j.ccr.2004.10.009
    21. J. Prunet, L. Grimaud. One or More CC Bond(s) Formed by Condensation: Condensation of Nonheteroatom-linked Functions, Halides, Chalcogen, or Nitrogen Functions. 2005, 669-722. https://doi.org/10.1016/B0-08-044655-8/00015-5
    22. C.K.-F. Chiu, M.A. Berliner, Z.B. Li. Alkenyl and Aryl Chalcogenides: Oxygen-based Functional Groups. 2005, 595-658. https://doi.org/10.1016/B0-08-044655-8/00035-0
    23. C.M. Timperley. Ketenes, Their Cumulene Analogs and Their S, Se, and Te Analogs. 2005, 573-604. https://doi.org/10.1016/B0-08-044655-8/00061-1
    24. B.R. Buckley. Carboxylic Esters and Lactones. 2005, 127-174. https://doi.org/10.1016/B0-08-044655-8/00093-3
    25. Benito Alcaide, Pedro Almendros. Chapter 4 Four-membered ring systems. 2005, 82-97. https://doi.org/10.1016/S0959-6380(05)80046-7
    26. Craig A. Merlic, Brandon C. Doroh. Amine‐Catalyzed Coupling of Aldehydes and Ketenes Derived from Fischer Carbene Complexes: Formation of β‐Lactones and Enol Ethers.. ChemInform 2003, 34 (47) https://doi.org/10.1002/chin.200347070
    Download PDF
    Go to The Journal of Organic Chemistry
    Get e-Alerts
    Get e-Alerts

    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2003, 68, 15, 6056–6059
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo034476n
    Published June 26, 2003
    Copyright © 2003 American Chemical Society
    Request reuse permissions

    Article Views

    527

    Altmetric

    -

    Citations

    26
    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.