Discipline of Inorganic Materials and Catalysis, Central Salt and Marine Chemicals Research Institute, Council of Scientific & Industrial Research, G. B. Marg, Bhavnagar 364 021, Gujarat, India.
J Org Chem. 2012 May 4;77(9):4375-84. doi: 10.1021/jo300349f. Epub 2012 Apr 22.
Recyclable chiral amide-based organocatalyst 5 efficiently catalyzed asymmetric Strecker reaction of various aromatic and aliphatic N-benzhydrylimines with ethyl cyanoformate as cyanide source at -10 °C to give a high yield (95%) of α-aminonitriles with excellent chiral induction (ee, up to 99%) with the added advantage of recyclability. Based on experimental observations a probable mechanism was proposed for this reaction. This protocol with catalyst 5 was extended for the synthesis of (R)-phenylalanine and pharmaceutically important drug intermediate (R)-3-phenylpropane-1,2-diamine in high yield with high enantioselectivity.
可回收的手性酰胺基有机催化剂 5 能高效催化各种芳香族和脂肪族 N-苯亚甲基腙与氰基甲酸乙酯的不对称 Streck 反应，在 -10°C 下以高产率（95%）得到α-氨基腈，对映选择性极好（ee 值高达 99%），而且具有可回收的优点。根据实验观察，提出了该反应的可能机理。该方案中使用催化剂 5 可以高产率和高对映选择性地合成（R）-苯丙氨酸和具有重要药用价值的药物中间体（R）-3-苯基-1,2-丙二胺。
