American Chemical Society
ol6b01203_si_001.pdf (3.44 MB)

Stereoselective Synthesis of Alkylidene Phthalides

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journal contribution
posted on 2016-06-16, 19:53 authored by Andrei Dragan, D. Heulyn Jones, Alan R. Kennedy, Nicholas C. O. Tomkinson
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.