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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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Official URL: https://doi.org/10.1021/acs.orglett.6b01203

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.

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:	03 Mar 2019 08:49
URI:	https://strathprints.strath.ac.uk/id/eprint/56647
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