22596-57-2Relevant articles and documents
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 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.
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
