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.).
Efficient Synthesis of Diarylmethylamines via Lewis Acid Catalyzed Friedel-Crafts Reactions of Donor-Acceptor Aziridines with N, N -Dialkylanilines
Kim, Sung-Gon,Kim, Yerin,Kwon, Yong Il
, p. 281 - 289 (2020)
A method for efficient and mild synthesis of diarylmethylamine scaffold, via Lewis acid catalyzed Friedel-Crafts reaction of donor-acceptor aziridines with N, N -dialkylanilines to afford a biologically important diarylmethylamine derivatives in high yields (up to 88percent), is presented. This reaction is suitable for the synthesis of various diarylmethylamine derivatives and has a broad scope for electron-rich arenes, including dimethoxybenzene.
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.
Highly stereoselective, one-pot synthesis of azetidines and 2,4-dioxo-1,3-diazabicyclo[3.2.0] compounds mediated by I2
Miao, Chun-Bao,Dong, Chun-Ping,Zhang, Min,Ren, Wen-Long,Meng, Qi,Sun, Xiao-Qiang,Yang, Hai-Tao
, p. 4329 - 4340 (2013/06/05)
We report here a convenient method to construct polysubstituted azetidines and 2,4-dioxo-1,3-diazabicyclo[3.2.0] compounds with high stereoselectivities in a one-pot reaction mediated by I2. The tetramethylguanidine (TMG)/I2-mediated formal [2 + 2] cycloaddition reaction of α-amidomalonate 1 with enones 2 affords functionalized azetidine derivatives 4 in moderate to good yields with high diastereoselectivity. When the α-ureidomalonate 5 is used instead of 1, 2,4-dioxo-1,3-diazabicyclo[3. 2.0]heptanes 8 and 2,4-dioxo-1,3-diazabicyclo[3.2.0]heptenes 9 can be prepared selectively through the control of solvent and temperature. 2,4-Dioxo-1,3- diazabicyclo[3.2.0]heptanes 8 can further undergo ring-opening reactions with different nucleophilic reagents to afford the corresponding polyfunctionalized azetidine derivatives 13-16 with high steroselectivities.
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
