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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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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.