Rising Stars in Organic Synthesis, Session 3: Constructive Ozonolysis: Capturing Primary Ozonides - presented by Prof. Andy Thomas | Cyclopropane Synthesis using Palladium Carbenes - presented by Prof. Sidney Wilkerson-Hill | Access to Previously "Inaccessible" Arynes Using Transition Metals - presented by Prof. Courtney Roberts | The use of C―H bond oxidations in the synthesis of natural products - presented by Prof. Emilio de Lucca Jr. | Sulfonylcyclopropanols as Modular Cyclopropanone Equivalents - presented by Prof. Vince Lindsay

Rising Stars in Organic Synthesis, Session 3

Prof. Andy ThomasProf. Courtney RobertsProf. Emilio de Lucca Jr.Prof. Sidney Wilkerson-HillProf. Vince Lindsay
Slide at 21:57
UNITED Thomas, Constructive Ozonolysis: Capturing Primary Ozonides (Batch) i-PrMgBr -130 C, CF2Cl2 -130 C, CF2Cl2 trans-Olefins 71 % 69 % cis-Olefins 64 % Arriaga, D. K.; Thomas, A. A., Nat Chem 2023, 15, 1262 Arriaga, D. K.; Kang, S.; Thomas, A. A. J. Org. Chem. 2023, 88, 13720
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References
  • 1.
    D. K. Arriaga and A. A. Thomas (2023) Capturing primary ozonides for a syn-dihydroxylation of olefins. Nature Chemistry
  • 2.
    D. K. Arriaga et al. (2023) Effect of Solvent on the Rate of Ozonolysis: Development of a Homogeneous Flow Ozonolysis Protocol. The Journal of Organic Chemistry
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Summary (AI generated)

Ventilated ethers, metox ethers, electron deficient groups chains, and tartrate can be made. Cysteine reactions can be done at lower temperatures. Terminal alkenes work well in these reactions. This method was applied to pharmaceutical agents such as the active ingredient in Mucinex and a pois precursor. The 11 disubstituted alkenes also work well.