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Direct stereospecific synthesis of unprotected N-H and N-Me aziridines from olefins

Jawahar L. Jat; Mahesh P. Paudyal; Hongyin Gao; Qing-Long Xu; Muhammed Yousufuddin; Deepa Devarajan; Daniel H. Ess; Lászĺo K̈urti; John R. Falck

(Profiled Authors: J R Falck; Laszlo Kurti)

Science. 2014;343(6166):61-65.

Abstract

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.


PMID: 24385626    

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