Highly Enantioselective Reductions of 2H-Azirines
Herein, we present the first highly enantioselective reduction of mono- and tri- substituted 2H-azirines mediated by a chiral copper-hydride complex. The reaction tolerates both alkylated and arylated 2H-azirines to afford free N-H aziridines in excellent yield (up to 96%) and enantioselectivity (up to 96% ee). A key finding was the stark difference in
Yinuo Zheng +4 more
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Lewis acid Mediated Aza-Diels-Alder Reactions and Asymmetric Alkylations of 2H-azirines
, 2004 This thesis describes the use of 2H-azirines, three-membered unsaturatednitrogen-containing heterocycles, as reactive intermediates ina number of Lewis acid promoted alkylations and Diels-Alderreactions providing synthetically useful aziridines. In order
Risberg, Erik
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Copper(II)-Catalyzed (3+2) Cycloaddition of 2H-Azirines to Six-Membered Cyclic Enols as a Route to Pyrrolo[3,2-c]quinolone, Chromeno[3,4-b]pyrrole, and Naphtho[1,8-ef]indole Scaffolds. [PDF]
Molecules, 2022 Sakharov PA +3 more
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Photochemically Induced 1,3-Dipolar Cycloadditions of 3-Amino-2H-azirines
, 1980 Irradiation of 3-(N-methylanilino)-2H-azirines in dimethoxyethane solution in the presence of dipolarophiles leads to five-membered heterocycles in 40-60% yield.
Stegmann, werner +2 more
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Transition-metal-free synthesis of substituted pyridines via ring expansion of 2-allyl-2H-azirines
, 2014 A new strategy to open the 2-allyl-2H-azirines by 1,8-diazabicyclo[5.4.0] undec-7-ene (DBU) promotion in metal-free conditions affording 1-azatrienes that in situ electrocyclize to the pyridines in good to excellent yields is reported.
Loh, Teck-Peng +5 more
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Molybdenum hexacarbonyl-induced reactions of 3-aryl-2h-azirines and acetylenes
, 1979 In the presence of molybdenum hexacarbonyl, 3-phenyl-2H-azirines and acetylene carboxylic acid esters react via the unusual splitting of the C,N-double bond to give 2H-pyrroles or ...
Inada, Akira +5 more
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, 2016 2H-azirines can serve as three-atom synthons by C-C bond cleavage, however, it involves a high energy barrier under thermal conditions (> 50.0 kcalmol (1)). Reported is a ruthenium-catalyzed [3+2+2] cycloaddition reaction of 2H-azirines with diynes, thus
Wan, Boshun +4 more
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DFT and AFIR study on the copper(i)-catalyzed mechanism of 5-enamine-trisubstituted-1,2,3-triazole synthesis via C-N cross-coupling and the origin of ring-opening of 2H-azirines. [PDF]
RSC Adv, 2021 Yu F, Zhou Z, Song J, Zhao Y.
europepmc +1 more source
Synthesis of α-Aminophosphonic Acid Derivatives Through the Addition of O- and S-Nucleophiles to 2H-Azirines and Their Antiproliferative Effect on A549 Human Lung Adenocarcinoma Cells. [PDF]
Molecules, 2020 Carramiñana V +3 more
europepmc +1 more source