posted on 2016-06-16, 19:53authored byAndrei 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.