The Aza‐Morita–Baylis–Hillman Reaction of <i>N</i>‐Thiophosphoryl Imines Catalyzed by 1,3,5‐Triaza‐7‐phosphaadamantane (PTA) –– Convenient Synthesis of α‐Methylene‐β‐Amino Ketone or Acid Derivatives

Abstract

Abstract In the presence of an effective air‐stable nucleophilic trialkylphosphane orgaocatalyst, 1,3,5‐triaza‐7‐phosphaadamantane, N ‐diethoxythiophosphorylimines 1 and N ‐diphenylthiophosphinoylimines 2 exhibited good reactivity in the methyl vinyl ketone or methyl acrylate based aza‐Morita–Baylis–Hillman reaction. The corresponding products were obtained in fair‐to‐excellent chemical yields. Moreover, the chiral‐imine‐induced diastereoselective aza‐MBH reaction was also realized with 90 % de . This reaction provides a convenient method for the synthesis of synthetically valuable α‐methylene‐β‐amino ketone or acid derivatives.(© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2007)