102535-89-7Relevant academic research and scientific papers
Rhodium(II)-catalyzed aziridinations and ch insertions with [N-(p-nitrobenzenesulfonyl)imino]phenyliodinane
Mueller, Paul,Baud, Corine,Jacquier, Yvan,Moran, Mary,Naegeli, Ivo
, p. 341 - 347 (1996)
The [Rh2(OAc)4]-catalyzed decomposition of NsN=IPh {[N-(p-nitrobenzenesulfonyl)imino]phenyliodinane} in the presence of olefins affords aziridines in yields of up to 85%. The aziridination of cis-hex-2-ene and cis-β-methylstyrene is stereospecific, but, cis-stilbene affords a 3:1 mixture of cis- and trans-aziridines in low yield. With chiral Rh(II) catalysts, optically active aziridines are formed having enantiomeric excesses of up to 73%. The NsN-IPh-[Rh2(OAc)4] system is also efficient for the allylic amination of olefins and for insertion into CH bonds, activated by phenyl or oxygen substituents.
Photo-induced aziridination of alkenes with N-sulfonyliminoiodinanes
Masakado, Sota,Kobayashi, Yusuke,Takemoto, Yoshiji
, p. 688 - 690 (2018)
Activation of N-sulfonyliminiodinanes was achieved by photo-irradiation at 375nm, which enabled the reaction with several alkenes to afford the corresponding aziridines. Mechanistic studies suggested that the reaction would proceed through a stepwise mech
Generation and Ring Opening of Aziridines in Telescoped Continuous Flow Processes
Hsueh, Nathanael,Clarkson, Guy J.,Shipman, Michael
supporting information, p. 3632 - 3635 (2015/07/28)
A simple method for the preparation of a variety of N-sulfonyl aziridines (10 examples) from 1,2-amino alcohols under continuous flow conditions is described. Using flow based methods, the aziridines can be further ring opened with oxygen, carbon, and hal
Stereoselective Lewis acid mediated (3+2) cycloadditions of N-H- and N-sulfonylaziridines with heterocumulenes
Craig, Robert A.,O'Connor, Nicholas R.,Goldberg, Alexander F. G.,Stoltz, Brian M.
supporting information, p. 4806 - 4813 (2014/05/06)
Alkyl and aryl isothiocyanates and carbodiimides are effective substrates in (3+2) cycloadditions with N-sulfonyl-2-substituted aziridines and 2-phenylaziridine for the synthesis of iminothiazolidines and iminoimidazolidines. Additionally, the stereoselec
Catalyst-free aziridination and unexpected homologation of aziridines from imines
Branco, Paula Serio,Raje, Vivek Prabhakar,Dourado, Jorge,Gordo, Joana
experimental part, p. 2968 - 2974 (2010/09/06)
Aziridination and unpredicted homologation reaction of N-sulfonylimines were achieved easily with a very simple, rapid and mild procedure through the use of diazomethane without the presence of any catalyst. The method represents an attractive alternative
Asymmetric N1 unit transfer to olefins with a chiral nitridomanganese complex: Novel stereoselective pathways to aziridines or oxazolines
Nishimura, Masaaki,Minakata, Satoshi,Takahashi, Toru,Oderaotoshi, Yoji,Komatsu, Mitsuo
, p. 2101 - 2110 (2007/10/03)
Chiral nitridomanganese complex 1 was found to be a highly potential N1 unit source for the asymmetric synthesis of aziridines and 2-oxazolines from olefins such as styrene and its derivatives. When sulfonyl chlorides were employed as activators of the complex in the presence of pyridine, pyridine N-oxide, and a silver salt, the reaction of olefins with complex 1 proceeded smoothly to afford the N-sulfonylated aziridines. The aziridination of styrene derivatives with complex 1 using 2-trimethylsilylethanesulfonyl chloride (SESC1) gave the N-SES-aziridines, which were easily converted into chiral N-unsubstituted aziridines. It was found that the reaction was applicable to the asymmetric synthesis of 2-oxazolines from olefins when acyl chlorides were employed as activators. Complex I provided an effective asymmetric environment for trans-disubstituted styrenes in the reaction (up to 92% ee). This is the first example of a direct asymmetric synthesis of 2-oxazolines from olefins. Additional experiments, conducted during the course of this investigation, suggest that the isomerization of the N-acylaziridine intermediate is involved in this reaction.
The rhodium(II)-catalyzed aziridination of olefins with {[(4- nitrophenyl)sulfonyl]imino}phenyl-λ3-iodane
Müller, Paul,Baud, Corine,Jacquier, Yvan
, p. 738 - 750 (2007/10/03)
The aziridination of olefins with {(4- nitrophenylsulfonyl)imino}phenyl-λ3-iodane, NsN=IPh (1c), in the presence of [Rh2(OAc)4] proceeds in yields of up to 85% when the olefin is used in large excess. Under optimized conditions, styrene (4a) is aziridinated with 1 equiv. of NsN=IPh (1c) in 64% yield with 2 mol% of catalyst. The aziridines derived from electron-rich olefins undergo ring-opening under the conditions of the aziridination and afford rearrangement products or pyrrolidines. The aziridination is sterospecific with 1,2-dialkyl- and 1,2-arylalkyl- disubstituted olefins, but nonstereospecific with stilbene. The ρ-value for aziridination of substituted styrenes iS -0.61. No ring-opened products are observed upon aziridination of vinylcyclopropanes. In the presence of chiral Rh(II) catalysts, the aziridination is enantioselective, affording an ee of 73% with cis-β-methylstyrene (4k) and Pirrungs [Rh2{(R)-(-)-bnp}4] catalyst. The experimental results are consistent with a one-step mechanism for transfer of the nitrenoid moiety from the catalyst to the olefin.
Iodine-catalyzed aziridination of alkenes using chloramine-T as a nitrogen source
Ando, Takeya,Kano, Daisuke,Minakata, Satoshi,Ryu, Ilhyong,Komatsu, Mitsuo
, p. 13485 - 13494 (2007/10/03)
Iodine was found to be an efficient catalyst for the aziridination of alkenes utilizing Chloramine-T (N-chloro-N-sodio-p-toluenesulfonamide) as a nitrogen source. For example, when two equivalents of styrene were added to Chloramine-T in the presence of a
