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

[img]
Preview
 Text (Dragan-etal-OL-2016-Stereoselective-synthesis-of-alklidene)
Dragan_etal_OL_2016_Stereoselective_synthesis_of_alklidene.pdf
Accepted Author Manuscript
Download (1MB)| Preview

    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.

    Creators(s): 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
    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:25 Jan 2021 03:36
    URI:https://strathprints.strath.ac.uk/id/eprint/56647
    Export data:
    CORE (COnnecting REpositories)