Synthesis of Phenyl Ring Substituted 4-Aryl-3,4-Dihydrocoumarines

Abstract

Asymmetric induction caused by 4-substituted oxazolidin-2-one type auxiliaries in reactions of N-cinnamoyloxazolidinones with phenylmagnesium bromide in the presence of CuBr×SMe2 catalyst were examined. Resulted 3,3-diarypropionic acid derivatives were converted into 6-hydroxy-4-phenyldihydrocoumarine via demethylation and subsequent pyrane ring closure. Hydroarylation of N-cinnamoyloxazolidinones with 1,3,5-trimethoxybenzene was performed affording 3,3-diarypropionic acid derivatives.