Density Functional Study on the Mechanism of Bicyclic Guanidine-Catalyzed Strecker Reaction
The Journal of Organic Chemistry2003Vol. 68(23), pp. 8786–8789
Citations Over TimeTop 13% of 2003 papers
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.
Related Papers
- → Guanidine hydrochloride as an organocatalyst for N-Boc protection of amino groups(2011)53 cited
- → The Reactions of Hydroiodide of 2‐Amino‐1‐substituted Guanidine Derivatives with Aromatic Isothiocyanates.(2002)1 cited
- → ChemInform Abstract: CYCLIZATION OF GUANIDINES WITH α,β‐UNSATURATED KETONES: IMPROVED SYNTHESIS OF 2‐AMINODIHYDROPYRIMIDINE DERIVATIVES CONTAINING A GUANIDINE MOIETY(1981)1 cited
- → ChemInform Abstract: Guanidine Hydrochloride as an Organocatalyst for N‐Boc Protection of Amino Groups.(2011)
- → ChemInform Abstract: The GAP Chemistry for Chiral N‐Phosphonyl Imine‐Based Strecker Reaction.(2011)