71535-50-7Relevant academic research and scientific papers
Ni-Catalyzed Carboxylation of Aziridines en Route to β-Amino Acids
Davies, Jacob,Janssen-Müller, Daniel,Zimin, Dmitry P.,Day, Craig S.,Yanagi, Tomoyuki,Elfert, Jonas,Martin, Ruben
supporting information, p. 4949 - 4954 (2021/04/07)
A Ni-catalyzed reductive carboxylation of N-substituted aziridines with CO2 at atmospheric pressure is disclosed. The protocol is characterized by its mild conditions, experimental ease, and exquisite chemo- and regioselectivity pattern, thus unlocking a new catalytic blueprint to access β-amino acids, important building blocks with considerable potential as peptidomimetics.
Iron(ii)-catalyzed intermolecular aziridination of alkenes employing hydroxylamine derivatives as clean nitrene sources
Berhal, Farouk,Grimaud, Laurence,Kirby, Georgina,Prestat, Guillaume,Vitale, Maxime R.
, p. 9428 - 9432 (2021/12/09)
The iron-catalyzed intermolecular aziridination of alkenes with hydroxylamine derivatives is described. Using simple iron(ii) sources and readily available ligands, the formal (2 + 1) cycloaddition process proved to be efficient on both styrenes and aliphatic alkenes, providing access to a wide range of aziridines. In these particularly sustainable reaction conditions, yields up to 89% could be obtained, with a catalyst loading which could be lowered to 5 mol% when the reaction was performed on large scale. Preliminary mechanistic studies suggest that both concerted and stepwise pathways are operating in this transformation. This journal is
Synthesis and hetero-Diels-Alder reactions of enantiomerically pure dihydro-1: H -azepines
Craig, Donald,Spreadbury, Samuel R. J.,White, Andrew J. P.
, p. 9803 - 9806 (2020/09/16)
Thermolysis of enantiomerically pure 3-substituted 7,7-dihalo-2-azabicyclo[4.1.0]heptanes in the presence of K2CO3 gives in good yields 2-alkyl-6-halo-1-tosyl-2,3-dihydro-1H-azepines. These undergo highly stereoselective [4+2] cycloaddition reactions with heterodienophiles and arylation/alkenylation under Suzuki conditions.
Synthesis of β-Phenethylamines via Ni/Photoredox Cross-Electrophile Coupling of Aliphatic Aziridines and Aryl Iodides
Steiman, Talia J.,Liu, Junyi,Mengiste, Amanuella,Doyle, Abigail G.
supporting information, p. 7598 - 7605 (2020/04/21)
A photoassisted Ni-catalyzed reductive cross-coupling between tosyl-protected alkyl aziridines and commercially available (hetero)aryl iodides is reported. This mild and modular method proceeds in the absence of stoichiometric heterogeneous reductants and uses an inexpensive organic photocatalyst to access medicinally valuable β-phenethylamine derivatives. Unprecedented reactivity was achieved with the activation of cyclic aziridines. Mechanistic studies suggest that the regioselectivity and reactivity observed under these conditions are a result of nucleophilic iodide ring opening of the aziridine to generate an iodoamine as the active electrophile. This strategy also enables cross-coupling with Boc-protected aziridines.
Carbon Isotope Labeling Strategy for β-Amino Acid Derivatives via Carbonylation of Azanickellacycles
Ravn, Anne K.,Vilstrup, Maria B. T.,Noerby, Peter,Nielsen, Dennis U.,Daasbjerg, Kim,Skrydstrup, Troels
supporting information, p. 11821 - 11826 (2019/08/16)
A series of 4-membered azametallacycles have been prepared by the oxidative addition of Ni(0) with aziridines. Stoichiometric 13C-labeled carbon monoxide could be efficiently incorporated via Ni-C bond insertion to generate air stable and isola
Cu-Catalyzed [3 + 3] Cycloaddition of Isocyanoacetates with Aziridines and Stereoselective Access to α,γ-Diamino Acids
Kok, Germaine Pui Yann,Yang, Hui,Wong, Ming Wah,Zhao, Yu
supporting information, p. 5112 - 5115 (2018/09/12)
We report herein an efficient Cu-catalyzed formal [3 + 3] cycloaddition of isocyanoacetates with readily available aziridines of different substitution patterns, which provides a practical access to valuable 1,4,5,6-tetrahydropyrimidine derivatives. In pa
Synthesis of tubuphenylalanine and epi-tubuphenylalanine via regioselective aziridine ring opening with carbon nucleophiles followed by hydroboration-oxidation of 1,1-substituted amino alkenes
Reddy, Ramesh B.,Dudhe, Premansh,Chauhan, Priyanka,Sengupta, Sagnik,Chelvam, Venkatesh
, p. 6946 - 6953 (2018/10/24)
An efficient synthesis of N-Boc-tubuphenylalanine benzyl ester (N-Boc-Tup-OBn, 1a) and N-Boc-epi-tubuphenylalanine benzyl ester (N-Boc-epi-Tup-OBn, 1b) is reported herein. Regioselective aziridine 4 ring opening with carbon nucleophiles followed by hydrob
Synthesis of indolines: Via a palladium/norbornene-catalyzed reaction of aziridines with aryl iodides
Liu, Ce,Liang, Yujie,Zheng, Nian,Zhang, Bo-Sheng,Feng, Yuan,Bi, Siwei,Liang, Yong-Min
supporting information, p. 3407 - 3410 (2018/04/05)
A Pd- and norbornene-catalyzed domino procedure has been developed to synthesize indoline compounds. This reaction provides efficient access to indolines by employing aryl iodides with aziridines as new electrophiles. The transformation is scalable and tolerates a range of functional groups.
Enantiodivergent Synthesis of (+)- and (?)-Pyrrolidine 197B: Synthesis of trans-2,5-Disubstituted Pyrrolidines by Intramolecular Hydroamination
Pérez, Sixto J.,Purino, Martín A.,Cruz, Daniel A.,López-Soria, Juan M.,Carballo, Rubén M.,Ramírez, Miguel A.,Fernández, Israel,Martín, Víctor S.,Padrón, Juan I.
supporting information, p. 15529 - 15535 (2016/10/13)
A highly efficient, diastereoselective, iron(III)-catalyzed intramolecular hydroamination/cyclization reaction involving α-substituted amino alkenes is described. Thus, enantiopure trans-2,5-disubstituted pyrrolidines and trans-5-substituted proline derivatives were synthesized by means of a combination of enantiopure starting materials, easily available from l-α-amino acids, with sustainable metal catalysts such as iron(III) salts. The scope of this methodology is highlighted in an enantiodivergent approach to the synthesis of both (+)- and (?)-pyrrolidine 197B alkaloids from l-glutamic acid. In addition, a computational study was carried out to gain insight into the complete diastereoselectivity of the transformation.
Achieving regio- and stereo-control in the fluorination of aziridines under acidic conditions
Okoromoba, Otome E.,Li, Zhou,Robertson, Nicole,Mashuta, Mark S.,Couto, Uenifer R.,Tormena, Cláudio F.,Xu, Bo,Hammond, Gerald B.
supporting information, p. 13353 - 13356 (2016/11/18)
We developed an efficient fluorination protocol that converts easily accessible aziridines into β-fluoroamines, which are important motifs in biologically active molecules. In contrast with traditional fluorination approaches, DMPU-HF has shown both highe
