• Login
    View Item 
    •   Home
    • Research
    • Articles
    • View Item
    •   Home
    • Research
    • Articles
    • View Item
    JavaScript is disabled for your browser. Some features of this site may not work without it.

    Browse

    All of KAUSTCommunitiesIssue DateSubmit DateThis CollectionIssue DateSubmit Date

    My Account

    Login

    Quick Links

    Open Access PolicyORCID LibguideTheses and Dissertations LibguideSubmit an Item

    Statistics

    Display statistics

    Highly enantio- and diastereoselective allylic alkylation of Morita-Baylis-Hillman carbonates with allyl ketones

    • CSV
    • RefMan
    • EndNote
    • BibTex
    • RefWorks
    Type
    Article
    Authors
    Tong, Guanghu
    Zhu, Bo
    Lee, Richmond
    Yang, Wenguo
    Tan, Davin
    Yang, Caiyun
    Han, Zhiqiang
    Yan, Lin
    Huang, Kuo-Wei cc
    Jiang, Zhiyong
    KAUST Department
    Biological and Environmental Sciences and Engineering (BESE) Division
    Chemical Science Program
    Homogeneous Catalysis Laboratory (HCL)
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2013-04-26
    Online Publication Date
    2013-04-26
    Print Publication Date
    2013-05-17
    Permanent link to this record
    http://hdl.handle.net/10754/562767
    
    Metadata
    Show full item record
    Abstract
    The asymmetric allylic alkylation of Morita-Baylis-Hillman (MBH) carbonates with allyl ketones has been developed. The α-regioselective alkylation adducts, containing a hexa-1,5-diene framework with important synthetic value, were achieved in up to 83% yield, >99% ee, and 50:1 dr by using a commercially available Cinchona alkaloid as the catalyst. From the allylic alkylation adduct, a cyclohexene bearing two adjacent chiral centers was readily prepared. © 2013 American Chemical Society.
    Citation
    Tong, G., Zhu, B., Lee, R., Yang, W., Tan, D., Yang, C., … Jiang, Z. (2013). Highly Enantio- and Diastereoselective Allylic Alkylation of Morita–Baylis–Hillman Carbonates with Allyl Ketones. The Journal of Organic Chemistry, 78(10), 5067–5072. doi:10.1021/jo400496z
    Sponsors
    Financial support from the National Natural Science Foundation of China (No. 21072044, 21202034), the Program for New Century Excellent Talents in University of Ministry of Education (NCET-11-0938), Excellent Youth Foundation of Henan Scientific Committee (114100510003) and Specialized Research Fund for the Doctoral Program of Higher Education (20104103120002) are greatly appreciated. We also thank Professor Choon-Hong Tan (Nanyang Technological University, Singapore) and Professor Fuwei Li (Lanzhou Institute of Chemical Physics, PR China) for their generous help in high resolution mass spectrum analysis.
    Publisher
    American Chemical Society (ACS)
    Journal
    The Journal of Organic Chemistry
    DOI
    10.1021/jo400496z
    PubMed ID
    23594149
    Relations
    Is Supplemented By:
    • [Dataset]
      Tong, G., Zhu, B., Lee, R., Yang, W., Tan, D., Yang, C., … Jiang, Z. (2013). CCDC 909467: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cczjcnh. DOI: 10.5517/cczjcnh HANDLE: 10754/624757
    ae974a485f413a2113503eed53cd6c53
    10.1021/jo400496z
    Scopus Count
    Collections
    Articles; Biological and Environmental Science and Engineering (BESE) Division; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

    entitlement

    Related articles

    • Direct asymmetric allylic alkenylation of N-itaconimides with Morita-Baylis-Hillman carbonates.
    • Authors: Yang W, Tan D, Li L, Han Z, Yan L, Huang KW, Tan CH, Jiang Z
    • Issue date: 2012 Aug 3
    • Direct asymmetric allylic alkylation of butenolides with Morita-Baylis-Hillman carbonates.
    • Authors: Cui HL, Huang JR, Lei J, Wang ZF, Chen S, Wu L, Chen YC
    • Issue date: 2010 Feb 19
    • Organocatalytic asymmetric allylic alkylation of oxindoles with Morita-Baylis-Hillman carbonates.
    • Authors: Jiang K, Peng J, Cui HL, Chen YC
    • Issue date: 2009 Jul 14
    • An organocatalytic asymmetric sequential allylic alkylation-cyclization of Morita-Baylis-Hillman carbonates and 3-hydroxyoxindoles.
    • Authors: Wang QL, Peng L, Wang FY, Zhang ML, Jia LN, Tian F, Xu XY, Wang LX
    • Issue date: 2013 Oct 21
    • Asymmetric organocatalytic allylic alkylation of Reissert compounds: a facile access to chiral 1,1-disubstituted 1,2-dihydroisoquinolines.
    • Authors: Qin TY, Liao WW, Zhang YJ, Zhang SX
    • Issue date: 2013 Feb 14
    DSpace software copyright © 2002-2022  DuraSpace
    Quick Guide | Contact Us | KAUST University Library
    Open Repository is a service hosted by 
    Atmire NV
     

    Export search results

    The export option will allow you to export the current search results of the entered query to a file. Different formats are available for download. To export the items, click on the button corresponding with the preferred download format.

    By default, clicking on the export buttons will result in a download of the allowed maximum amount of items. For anonymous users the allowed maximum amount is 50 search results.

    To select a subset of the search results, click "Selective Export" button and make a selection of the items you want to export. The amount of items that can be exported at once is similarly restricted as the full export.

    After making a selection, click one of the export format buttons. The amount of items that will be exported is indicated in the bubble next to export format.