Application of 27492-84-8, As an important bridge between the micro and macro material world, chemistry is one of the main methods and means for humans to understand and transform the material world. 27492-84-8, Name is Methyl 4-amino-2-methoxybenzoate, SMILES is O=C(OC)C1=CC=C(N)C=C1OC, belongs to esters-buliding-blocks compound. In a article, author is Fulton, Tyler J., introduce new discover of the category.
Global Diastereoconvergence in the Ireland-Claisen Rearrangement of Isomeric Enolates: Synthesis of Tetrasubstituted alpha-Amino Acids
A dual experimental/theoretical investigation of the Ireland-Claisen rearrangement of tetrasubstituted alpha-phthalimido ester enolates to afford alpha-tetrasubstituted, beta-trisubstituted alpha-amino acids (generally >20:1 dr) is described. For trans allylic olefins, the Z- and E-enol ethers proceed through chair and boat transition states, respectively. For cis allylic olefins, the trend is reversed. As a result, the diastereochemical outcome of the reaction is preserved regardless of the geometry of the enolate or the accompanying allylic olefin. We term this unique convergence of all possible olefin isomers global diastereoconvergence. This reaction manifold circumvents limitations in present-day technologies for the stereoselective enolization of alpha,alpha-disubstituted allyl esters. Density functional theory paired with state-of-the-art local coupled-cluster theory (DLPNO-CCSD(T)) was employed for the accurate determination of quantum mechanical energies.
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