Fe-catalyzed synthesis of substituted N-aryl oxazolidines

Abstract

A novel iron-catalyzed synthesis of substituted N-aryl oxazolidines was developed via C–N bond formation and methylenation. The reaction of aryl hydroxylamines with allyl alcohols, in the presence of formaldehyde or its equivalents, afforded variety of oxazolidine heterocycles in very good yields. This catalytic method is most effective for para-substituted aryl hydroxylamines and 3-methyl allyl alcohols. Furthermore, acid catalyzed demethylenation of oxazolidines allowed access to N-aryl amino alcohols in good yields.