1022820-87-6Relevant articles and documents
An Approach to α- and β-Amino Peroxides via Lewis Acid Catalyzed Ring Opening-Peroxidation of Donor-Acceptor Aziridines and N-Activated Aziridines
Singh, Kuldeep,Kumar, Pramod,Jagadeesh, Chenna,Patel, Manveer,Das, Dinabandhu,Saha, Jaideep
, p. 4130 - 4137 (2020)
Site-selective ring-opening process of two different aziridine classes with hydroperoxide is described herein that provides access to various α- and β-amino and α-(imino)-peroxy compounds. This strain-release-driven peroxide addition to aziridines represents an alternative approach for entries to biologically significant heteroatom substituted organic peroxides and complements existing methods in the field. The peroxide products obtained by this method displayed a different reactivity during peroxide-specific rearrangement processes promoted by either acid or base. Mechanistic studies and useful synthetic elaboration of the products have also been presented. (Figure presented.).
Copper-Catalyzed Annulation of Oxime Acetates with α-Amino Acid Ester Derivatives: Synthesis of 3-Sulfonamido/Imino 4-Pyrrolin-2-ones
Miao, Chun-Bao,Zheng, An-Qi,Zhou, Li-Jin,Lyu, Xinyu,Yang, Hai-Tao
supporting information, p. 3381 - 3385 (2020/04/21)
A copper-catalyzed annulation of oxime acetates and α-amino acid ester derivatives for the easy preparation of 4-pyrrolin-2-ones bearing a 3-amino group has been developed. This process features the oxidation of amines with oxime esters as the internal oxidant to produce the active 1,3-dinucleophilic and 1,2-dielectrophilic species concurrently. The subsequent nucleophilic cyclization realizes the efficient construction of 4-pyrrolin-2-one derivatives.
Copper(II) triflate catalyzed amination of 1,3-dicarbonyl compounds
Ton, Thi My Uyen,Himawan, Fanny,Chang, Joyce Wei Wei,Chan, Philip Wai Hong
supporting information, p. 12020 - 12027 (2012/10/29)
A method to prepare α,α-acyl amino acid derivatives efficiently by Cu(OTf)2+1,10-phenanthroline (1,10-phen)-catalyzed amination of 1,3-dicarbonyl compounds with PhI=NSO2Ar is described. The mechanism is thought to initially involve aziridination of the enolic form of the substrate, formed in situ through coordination to the Lewis acidic metal catalyst, by the putative copper-nitrene/imido species generated from the reaction of the metal catalyst with the iminoiodane source. Subsequent ring opening of the resultant aziridinol adduct under the Lewis acidic conditions then provided the α-aminated product. The utility of this method was exemplified by the enantioselective synthesis of a precursor of 3-styryl-2-benzoyl-L-alanine. Copyright
