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 (https://doi.org/10.1021/acs.orglett.6b01203)

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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:24 Sep 2022 02:16
    URI:https://strathprints.strath.ac.uk/id/eprint/56647
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