Radical Redox-Relay Catalysis: Formal [3+2] Cycloaddition of N-Acylaziridines and Alkenes
We report Ti-catalyzed radical formal [3+2] cycloadditions of N-acylaziridines and alkenes. This method provides an efficient approach to the synthesis of pyrrolidines, structural units prevalent in bioactive compounds and organocatalysts, from readily available starting materials. The overall redox-neutral reaction was achieved via a redox-relay mechanism, which harnesses radical intermediates for selective C - N bond cleavage and formation.
Hao, Wei,Wu, Xiangyu,Sun, James Z.,Siu, Juno C.,Macmillan, Samantha N.,Lin, Song
supporting information
p. 12141 - 12144
(2017/09/12)
Experimental and theoretical rearrangement of N-acyl-2,2- dimethylaziridines in acidic medium
The acid isomerization of N-acyl-2,2-dimethylaziridines 1 in concentrated sulfuric acid at room temperature leads to oxazolines 2 but the neutral hydrolysis of 1 in pure water at room temperature leads to amidoalcohols 3. However, the use of aqueous solutions of H2SO4 at different concentrations at room temperature leads to a mixture of oxazolines 2, amidoalcohols 3 and allylamides 4 with yields depending on the acidity of the medium and the nature of the acyl group. A mechanism has been suggested to explain the formation of these three products. DFT calculations employing the Gaussian 09 program with DFT/B3LYP methods and 6-311++G(2d,2p) basis set were carried out which gave the most stable geometry as well as their atomic charge distributions of compounds 1-4. [Figure not available: see fulltext.]
NOVEL BICYCLIC SULFONAMIDES FOR USE AS GLUCOCORTICOID RECEPTOR MODULATORS IN THE TREATMENT OF INFLAMMATORY DISEASES
Compounds of formula (I): or a pharmaceutically acceptable salt thereof; compositions comprising them, processes for preparing them and their use in medical therapy (for example modulating the glucocorticoid receptor in a warm blooded animal).
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Page/Page column 70-71
(2008/06/13)
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