22596-57-2Relevant academic research and scientific papers
Asymmetric substitution at the tetrasubstituted chiral carbon: Catalytic ring-opening alkylation of racemic 2,2-disubstituted aziridines with 3-substituted oxindoles
Ohmatsu, Kohsuke,Ando, Yuichiro,Ooi, Takashi
, p. 18706 - 18709 (2013)
A highly diastereo- and enantioselective ring-opening alkylation of racemic 2,2-disubstituted aziridines with 3-substituted oxindoles is achieved under the catalysis of a chiral 1,2,3-triazolium salt. This reaction represents a hitherto unknown, catalytic
Direct N-H/ N-Me Aziridination of Unactivated Olefins Using O-(Sulfonyl)hydroxylamines as Aminating Agents
Sabir, Shekh,Pandey, Chandra Bhan,Yadav, Ajay K.,Tiwari, Bhoopendra,Jat, Jawahar L.
, p. 12255 - 12260 (2018/09/27)
Unactivated aziridines are the core substructures in a plethora of bioactive natural products and serve as building blocks in organic synthesis. Despite this, very limited methods are available to access them directly from olefins, as most of the known me
Direct stereospecific synthesis of unprotected N-H and N-Me aziridines from olefins
Jat, Jawahar L.,Paudyal, Mahesh P.,Gao, Hongyin,Xu, Qing-Long,Yousufuddin, Muhammed,Devarajan, Deepa,Ess, Daniel H.,Kurti, Laszlo,Falck, John R.
, p. 61 - 65 (2014/03/21)
Despite the prevalence of the N-H aziridine motif in bioactive natural products and the clear advantages of this unprotected parent structure over N-protected derivatives as a synthetic building block, no practical methods have emerged for direct synthesis of this compound class from unfunctionalized olefins. Here, we present a mild, versatile method for the direct stereospecific conversion of structurally diverse mono-, di-, tri-, and tetrasubstituted olefins to N-H aziridines using O-(2,4-dinitrophenyl)hydroxylamine (DPH) via homogeneous rhodium catalysis with no external oxidants. This method is operationally simple (i.e., one-pot), scalable, and fast at ambient temperature, furnishing N-H aziridines in good-to-excellent yields. Likewise, N-alkyl aziridines are prepared from N-alkylated DPH derivatives. Quantum-mechanical calculations suggest a plausible Rh-nitrene pathway.
Aziridines in one step from hydantoins via Red-Al mediated ring-contraction
Von Kieseritzky, Fredrik,Lindstroem, Johan
experimental part, p. 4558 - 4561 (2011/09/20)
We have developed a new method to synthesize aziridines from their corresponding hydantoins in one step using an excess of Red-Al overnight in refluxing toluene. This allows direct access to N-H aziridines without the need for protecting group strategies.
METHOD FOR SYNTHESIZING AN N-UNSUBSTITUTED OR N-SUBSTITUTED AZIRIDINE
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Page/Page column 5, (2010/08/07)
Process for preparing an N-unsubstituted or N-substituted aziridine of the formula which comprises reacting an olefin of the formula I where R1 to R5 are each, independently of one another, hydrogen, a linear or branched alkyl radica
A micellar iodide-catalyzed synthesis of unprotected aziridines from styrenes and ammonia
Varszegi, Csaba,Ernst, Martin,Van Laar, Frederik,Sels, Bert F.,Schwab, Ekkehard,De Vos, Dirk E.
, p. 1477 - 1480 (2008/12/22)
(Chemical Equation Presented) Aziridines from ammonia: Unprotected aziridines are formed from styrenes in one catalytic step. Ammonia is incorporated directly using an aqueous micellar solution containing bleach as oxidant and substoichiometric amounts of
Activation of manganese nitrido complexes by Bronsted and Lewis acids. Crystal structure and asymmetric alkene aziridination of a chiral salen manganese nitrido complex
Ho, Chi-Ming,Lau, Tai-Chu,Kwong, Hoi-Lun,Wong, Wing-Tak
, p. 2411 - 2413 (2007/10/03)
Styrene is readily converted to 2-phenylaziridine by salen manganese(v) nitrido complexes in the presence of Bronsted or Lewis acids such as F3CCO2H or BF3, the crystal structure of a chiral manganese nitrido complex that
