5440-40-4Relevant articles and documents
Minisci-Type Alkylation of N-Heteroarenes by N-(Acyloxy)phthalimide Esters Mediated by a Hantzsch Ester and Blue LED Light
Kyne, Sara Helen,Li, Jiacheng,Siang Tan, Suan,Wai Hong Chan, Philip
supporting information, (2022/01/11)
A synthetic method that enables the Hantzsch ester-mediated Minisci-type C2-alkylation of quinolines, isoquinolines and pyridines by N-(acyloxy)phthalimide esters (NHPI) under blue LED (light emitting diode) light (456 nm) is described. Achieved under mild reaction conditions at room temperature, the metal-free synthetic protocol was shown to be applicable to primary, secondary and tertiary NHPIs to give the alkylated N-heterocyclic products in yields of 21–99%. On introducing a chiral phosphoric acid, an asymmetric version of the reaction was also realised and provided product enantiomeric excess (ee) values of 53–99%. The reaction mechanism was delineated to involve excitation of an electron-donor acceptor (EDA) complex, formed from weak electrostatic interactions between the Hantzsch ester and NHPI, which generates the posited radical species of the redox active ester that undergoes addition to the N-heterocycle.
Direct Synthesis of Free α-Amino Acids by Telescoping Three-Step Process from 1,2-Diols
Inada, Haruki,Shibuya, Masatoshi,Yamamoto, Yoshihiko
supporting information, p. 709 - 713 (2019/01/25)
A practical telescoping three-step process for the syntheses of α-amino acids from the corresponding 1,2-diols has been developed. This process enables the direct synthesis of free α-amino acids without any protection/deprotection step. This method was also effective for the preparation of a 15N-labeled α-amino acid. 1,2-Diols bearing α,β-unsaturated ester moieties afforded bicyclic α-amino acids through intramolecular [3 + 2] cycloadditions. A preliminary study suggests that the resultant α-amino acids are resolvable by aminoacylases with almost complete selectivity.
METHOD OF AMIDOCARBONYLATION REACTION
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Page/Page column 11, (2008/06/13)
A novel method of an amidocarbonylation reaction among an aldehyde compound, an amide compound, and carbon monoxide, which comprises using a palladium-supporting crosslinked-polymer composition containing palladium clusters having a major-axis length of 20 nm or shorter to conduct the amidocarbonylation reaction. Thus, an N-acyl-±-amino acid can be more efficiently and selectively synthesized in a clean reaction system. Also provided is a catalyst for use in the method.