• Login
    View Item 
    •   Home
    • Faculty/ Researcher Works
    • Faculty/ Researcher Works
    • View Item
    •   Home
    • Faculty/ Researcher Works
    • Faculty/ Researcher Works
    • View Item
    JavaScript is disabled for your browser. Some features of this site may not work without it.

    Browse

    All of TUScholarShareCommunitiesDateAuthorsTitlesSubjectsGenresThis CollectionDateAuthorsTitlesSubjectsGenres

    My Account

    LoginRegister

    Help

    AboutPoliciesHelp for DepositorsData DepositFAQs

    Statistics

    Display statistics

    Acceleration of an aromatic claisen rearrangement via a designed spiroligozyme catalyst that mimics the ketosteroid isomerase catalytic dyad

    • CSV
    • RefMan
    • EndNote
    • BibTex
    • RefWorks
    Thumbnail
    Name:
    Acceleration of an aromatic ...
    Size:
    4.597Mb
    Format:
    PDF
    Download
    Genre
    Journal Article
    Date
    2014-03-12
    Author
    Parker, MFL
    Osuna, S
    Bollot, G
    Vaddypally, S
    Zdilla, MJ
    Houk, KN
    Schafmeister, CE
    Subject
    Biomimetic Materials
    Catalysis
    Coumarins
    Hydrogen Bonding
    Methylation
    Models, Molecular
    Steroid Isomerases
    Permanent link to this record
    http://hdl.handle.net/20.500.12613/5891
    
    Metadata
    Show full item record
    DOI
    10.1021/ja409214c
    Abstract
    A series of hydrogen-bonding catalysts have been designed for the aromatic Claisen rearrangement of a 1,1-dimethylallyl coumarin. These catalysts were designed as mimics of the two-point hydrogen-bonding interaction present in ketosteroid isomerase that has been proposed to stabilize a developing negative charge on the ether oxygen in the migration of the double bond.1 Two hydrogen bond donating groups, a phenol alcohol and a carboxylic acid, were grafted onto a conformationally restrained spirocyclic scaffold, and together they enhance the rate of the Claisen rearrangement by a factor of 58 over the background reaction. Theoretical calculations correctly predict the most active catalyst and suggest that both preorganization and favorable interactions with the transition state of the reaction are responsible for the observed rate enhancement. © 2014 American Chemical Society.
    Citation to related work
    American Chemical Society (ACS)
    Has part
    Journal of the American Chemical Society
    ADA compliance
    For Americans with Disabilities Act (ADA) accommodation, including help with reading this content, please contact scholarshare@temple.edu
    ae974a485f413a2113503eed53cd6c53
    http://dx.doi.org/10.34944/dspace/5873
    Scopus Count
    Collections
    Faculty/ Researcher Works

    entitlement

     
    DSpace software (copyright © 2002 - 2021)  DuraSpace
    Temple University Libraries | 1900 N. 13th Street | Philadelphia, PA 19122
    (215) 204-8212 | scholarshare@temple.edu
    Open Repository is a service operated 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.

    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.