Journal
SCIENCE
Volume 343, Issue 6166, Pages 61-65Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.1245727
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Funding
- NIH [GM31278, DK38226]
- Robert A. Welch Foundation [GL625910, I-1764]
- UT Southwestern Endowed Scholars in Biomedical Research Program (W. W. Caruth Jr. Endowed Scholarship in Biomedical Research)
- American Chemical Society-Petroleum Research Fund [51707-DNI1]
- American Cancer Society and Simmons Cancer Center Institutional Research Grant (New Investigator Award in Cancer Research) [ACS-IRG 02-196]
- UT Arlington
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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.
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