Stereochemical study on cyclic acetal formation during anodic oxidation of naphthalene derivatives by transformation of chiral alcohol to achiral acetal

Abstract

A novel stereochemical approach is employed in anodic oxidation of naphthalene derivatives to discriminate the intramolecular radical addition vs. intermolecular radical addition paths; the contribution of the latter is revealed to be important, judging from the stereodifferentiating addition of MeOH at C-4 during the anodic oxidation of (1′S,3′R)-1-(3′-hydroxy-1′-methylbutoxy)-4-methylnaphthalene.