title: Density functional study on the mechanism of bicyclic guanidine-catalyzed Strecker reaction.
abstract: As a direct and viable synthesis of amino acids, the small organic molecule catalyzed asymmetric Strecker reactions have been explored successfully in recent years. For these catalysts, the active sites may be a guanidine group or similarly a urea group. In an effort to elucidate the reaction mechanism, we have investigated the bicyclic guanidine-catalyzed Strecker reaction of HCN and methanimine using density functional theory with the B3LYP method. Assisted by guanidine, two competitive pathways to aminoacetonitrile were rationalized. The aminoisoacetonitrile may not form due to the instability of the product.
authors: Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, P. R. China 116023.
authors: Jing
authors: J
authors: Li
authors: Wan-Yi
authors: WY
authors: Jiang
authors: Ke-Li
authors: KL
authors: Han
authors: Guo-Zhong
authors: GZ
authors: He
authors: Can
authors: C
authors: Li
mesh_terms: D000607:Aminoacetonitrile / Q000737:chemistry; D002384:Catalysis; D019791:Guanidine / Q000737:chemistry*; D006856:Hydrogen Cyanide / Q000737:chemistry; D008958:Models, Molecular
chemical_list: D006856:Hydrogen Cyanide; D000607:Aminoacetonitrile; D019791:Guanidine