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: https://orcid.org/0000-0002-0170-753X

Kennedy, Alan R. ORCID: https://orcid.org/0000-0003-3652-6015

Tomkinson, Nicholas C. O. ORCID: https://orcid.org/0000-0002-5509-0133

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• Item metadata

  Item type:	Article
  ID code:	56647
  Dates:	Date Event 17 July 2016 Published 12 June 2016 Accepted
  Subjects:	Science > Chemistry
  Department:	Faculty of Science > Pure and Applied Chemistry
  Depositing user:	Pure Administrator
  Date deposited:	13 Jun 2016 14:55
  Last modified:	11 Nov 2024 11:26
  URI:	https://strathprints.strath.ac.uk/id/eprint/56647