Stereoselective synthesis of alkylidene phthalides

Dragan, Andrei and Jones, D. Heulyn and Kennedy, Alan R. and Tomkinson, Nicholas C. O. (2016) Stereoselective synthesis of alkylidene phthalides. Organic Letters, 18. pp. 3086-3089. ISSN 1523-7060

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    Abstract

    The N,O-diacylhydroxylamine derivative 4 has been prepared and its reactivity with nucleophiles investigated. On reaction with lithium enolates of cyclic or acyclic ketones, 4 is converted stereoselectively to the corresponding alkylidene phthalide. The stereochemical outcome of the transformation can be modified by changing the polarity of the reaction medium and the products isomerized under acidic conditions.

    ORCID iDs

    Dragan, Andrei ORCID logoORCID: https://orcid.org/0000-0002-0170-753X, Jones, D. Heulyn, Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015 and Tomkinson, Nicholas C. O. ORCID logoORCID: https://orcid.org/0000-0002-5509-0133;
    • Item type:Article
      ID code:56647
      Dates:
      Date
      Event
      17 July 2016
      Published
      12 June 2016
      Accepted
      Keywords:drug discovery, alkylidene phthalides, isobenzofuranone, Chemistry, Chemistry(all)
      Subjects:Science > Chemistry
      Department:Faculty of Science > Pure and Applied Chemistry
      Depositing user: Pure Administrator
      Date deposited:13 Jun 2016 14:55
      Last modified:09 Oct 2021 00:51
      URI:https://strathprints.strath.ac.uk/id/eprint/56647
    CORE (COnnecting REpositories)