52562-19-3Relevant articles and documents
PHOTOCHEMICAL SYNTHESIS OF MARMYCIN ANALOGUES THROUGH A NEW PHOTOCHEMICAL REACTION INVOLVING CARBONYL COMPOUNDS
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Paragraph 00112-00115, (2021/11/13)
Photochemical reactivity of carbonyl compounds leading to the synthesis of the Marmycin core is described. The photochemical reactivity involves an excited state reaction that provides convenient access to bicyclic compounds. The disclosed reactivity is a
Synthesis of 1-Amino-2,2,2-trifluoroalkylphosphonates from Alkene-Tethered Trifluoroacetimidoyl Chlorides
Rodríguez, José F.,Zhang, Anji,Arora, Ramon,Lautens, Mark
supporting information, p. 7540 - 7544 (2021/10/12)
The reaction of alkene-tethered trifluoroacetimidoyl chlorides with trialkyl phosphites furnishes 1-amino-2,2,2-trifluoroalkylphosphonates. The products were generated in moderate to good yields, and the scalability of this process was showcased. Partial hydrolysis of the phosphonate moiety was achieved. The cyclization is proposed to occur via formation of an imidoyl phosphonate intermediate that becomes susceptible to nucleophilic attack at nitrogen through the strong electron-withdrawing groups at the imidoyl carbon.
Uncovering New Excited State Photochemical Reactivity by Altering the Course of the de Mayo Reaction
Kandappa, Sunil Kumar,Valloli, Lakshmy Kannadi,Jockusch, Steffen,Sivaguru, Jayaraman
supporting information, p. 3677 - 3681 (2021/04/07)
An unprecedented and previously unknown photochemical reactivity of 1,3-dicarbonyl compounds is observed with amino-alkenes leading to dihydropyrans. This novel photochemical reactivity changes the established paradigm related to the De Mayo reaction between 1,3-dicarbonyl compounds and alkenes. This new reaction allows convenient access to the Marmycin core in a single step from commercially available reactants. The origin and scope of this new photoreaction is detailed with preliminary photophysical and mechanistic investigations.