Sulfonium ylides 7. Influence of substituents in the imide fragment on the regioselectivity of intramolecular cyclization of phthalimido-containing keto-stabilized sulfonium ylides

Article abstract of DOI:10.1007/BF02503783

The intramolecular cyclization of keto-stabilized sulfonium ylides obtained from β-alanine and containing various imide fragments was studied. On heating in toluene in the presence of PhCO₂H, ylides containing a phthalimide moiety are converted into indolizidine-2,6-dione derivatives, whereas those incorporating a 4-methyl-1,2,3,6-tetrahydrophthalimide or pyrrolidine-2,5-dione moieties do not undergo cyclization.