Catalytic Asymmetric Synthesis Using Feedstocks: AnEnantioselective Route to 2-Arylpropionic Acids and 1-ArylethylAmines via Hydrovinylation of Vinyl Arenes

摘要

A three-step procedure for the synthesis of 2-arylpropionic acids (profens) from vinyl arenes in nearlyenantiomerically pure form has been developed. Excellent yields (>97%), regioselectivities (>99%),and enantioselectivities (>97% ee) for the desired branched products were obtained in the asymmetrichydrovinylation reactions of vinyl arenes, and the products from these reactions were transformed into2-arylpropionic acids via oxidative degradation. Subsequent Curtius or Schmidt rearrangements of theseacids provided highly valued 1-arylethyl amines, including a prototypical primary amine with an a-chiraltertiary N-alkyl group, in very good yields.