6372-57-2Relevant academic research and scientific papers
I2/TBHP mediated diastereoselective synthesis of spiroaziridines
Ashitha, Kizhakkan Thiruthi,Vinaya, Puthiya Purayil,Krishna, Ajay,Vincent, Deepthy Cheeran,Jalaja, Renjitha,Varughese, Sunil,Somappa, Sasidhar Balappa
supporting information, p. 1588 - 1593 (2020/03/06)
Eventhough spiroheterocycles are considered as emerging drug candidates, synthesis of spiroaziridines has not been well explored so far. Herein, we disclose an efficient I2/TBHP mediated diastereoselective synthesis of N-alkyl spiroaziridines from primary amines and easily accessible α,β-unsaturated ketones. The reaction is also compatible for the synthesis of 2-aroylaziridines.
Oxygenation of Simple Olefins through Selective Allylic C?C Bond Cleavage: A Direct Approach to Cinnamyl Aldehydes
Liu, Jianzhong,Wen, Xiaojin,Qin, Chong,Li, Xinyao,Luo, Xiao,Sun, Ao,Zhu, Bencong,Song, Song,Jiao, Ning
supporting information, p. 11940 - 11944 (2017/09/20)
A novel metal-free allylic C?C σ-bond cleavage of simple olefins to give valuable cinnamyl aldehydes is reported. 1,2-Aryl or alkyl migration through allylic C?C bond cleavage occurs in this transformation, which is assisted by an alkyl azide reagent. This method enables O-atom incorporation into simple unfunctionalized olefins to construct cinnamyl aldehydes. The reaction features simple hydrocarbon substrates, metal-free conditions, and high regio- and stereoselectivity.
A Lewis acid/metal amide hybrid as an efficient catalyst for carbon-carbon bond formation
Yamashita, Yasuhiro,Saito, Yuki,Imaizumi, Takaki,Kobayashi, Shu
, p. 3958 - 3962 (2014/10/15)
While Lewis acids and metal amides are among the most frequently used metal species, they are believed to be incompatible when combined. Here we describe a Lewis acid/metal amide hybrid, which contains electron-withdrawing groups and basic and bulky nitro
Selective transformation of N-(propargylic)hydroxylamines into 4-isoxazolines and acylaziridines promoted by metal salts
Wada, Norihiro,Kaneko, Kentaro,Ukaji, Yutaka,Inomata, Katsuhiko
scheme or table, p. 440 - 442 (2011/06/23)
Cyclization of N-(propargylic)hydroxylamines catalyzed by AgBF4 afforded the corresponding 4-isoxazolines in good yields. Copper salts were found to promote the further transformation to acylaziridines. The combined use of AgBF4 and CuCl realiz
Dicobalt Octacarbonyl Promoted Rearrangement of 4-Isoxazolines to Acylaziridines: Dramatic Rate Acceleration with Very High Substrate Tolerance
Ishikawa, Teruhiko,Kudoh, Takayuki,Yoshida, Juri,Yasuhara, Ayako,Manabe, Shinobu,Saito, Seiki
, p. 1907 - 1910 (2007/10/03)
(Matrix Presented) Dicobalt octacarbonyl [Co2(CO)8] in acetonitrile at 75 °C triggers the cleavage of the N-O bond of 4-isoxazolines (1) to bring about the valence rearrangement to 2-acylaziridines (2). The isoxazolines were stable a
Unusual reactivity of cis-2-benzoyl-1-benzyl-3-phenylaziridine with p-nucleophiles - Ring opening vs. the Abramov reaction
Wroblewski, Andrzej E.,Maniukiewicz, Waldemar,Karolczak, Wieslawa
, p. 1433 - 1437 (2007/10/03)
Thermal (80 °C) addition of dimethyl phosphite to cis-2-benzoyl-1-benzyl-3-phenylaziridine occurred exclusively at C(3) with concomitant cleavage of the C(2)-C(3) bond. The carbonyl group in the aminoketone produced under these conditions was reduced with hydrogen over Pearlman's catalyst with low (20%) diastereoselectivity, while good (80%) de was observed in the NaBH4 reduction as a result of the 1,4-asymmetric induction. The products of the Abramov reaction of the title compound were obtained (de 92%) when CsF was used as catalyst.
A Rapid Synthesis of Aziridine Derivatives over Bentonite in 'Dry Media'
Saoudi, Aicha,Hamelin, Jack,Benhaoua, Hadj
, p. 492 - 493 (2007/10/03)
Functionalized aziridines are synthesized from dibromo compounds and primary aliphatic amines in the absence of solvent over bentonite as a solid support; in some examples microwave activation is compared to normal heating.
