Stereoselective synthesis of alkylidene phthalides

Andrei Dragan, D. Heulyn Jones, Alan R. Kennedy, Nicholas C. O. Tomkinson

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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.
Original languageEnglish
Pages (from-to)3086-3089
Number of pages4
JournalOrganic Letters
Volume18
DOIs
Publication statusPublished - 17 Jul 2016

Keywords

  • drug discovery
  • alkylidene phthalides
  • isobenzofuranone

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