An article Global Diastereoconvergence in the Ireland-Claisen Rearrangement of Isomeric Enolates: Synthesis of Tetrasubstituted alpha-Amino Acids WOS:000605189000037 published article about DIASTEREOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ESTERS; BOAT in [Fulton, Tyler J.; Cusumano, Alexander Q.; Alexy, Eric J.; Du, Yun E.; Stoltz, Brian M.] CALTECH, Warren & Katharine Schlinger Lab Chem & Chem Engn, Div Chem & Chem Engn, Pasadena, CA 91125 USA; [Zhang, Haiming] Genentech Inc, Small Mol Proc Chem, San Francisco, CA 94080 USA; [Houk, K. N.] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA in 2020, Cited 35. The Name is 2-Phenylbutanoic acid. Through research, I have a further understanding and discovery of 90-27-7. Application In Synthesis of 2-Phenylbutanoic acid
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.
About 2-Phenylbutanoic acid, If you have any questions, you can contact Fulton, TJ; Cusumano, AQ; Alexy, EJ; Du, YE; Zhang, HM; Houk, KN; Stoltz, BM or concate me.. Application In Synthesis of 2-Phenylbutanoic acid
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