On January 26, 2022, Paulisch, Tiffany O.; Mai, Lukas A.; Strieth-Kalthoff, Felix; James, Michael J.; Henkel, Christian; Guldi, Dirk M.; Glorius, Frank published an article.Application In Synthesis of Methyl 2-cyclopentanonecarboxylate The title of the article was Dynamic Kinetic Sensitization of β-Dicarbonyl Compounds-Access to Medium-Sized Rings by De Mayo-Type Ring Expansion. And the article contained the following:
Herein, we present a photocatalyzed two-carbon ring expansion of β-dicarbonyl compounds with unactivated olefins that provides facile access to medium-sized rings. Selective sensitization of the substoichiometric enol tautomer enables reactivity of substrates incompatible with the classical De Mayo reaction conditions. Key to success was the identification of the metal-based sensitizer fac-[Ir(CF3-pmb)3], which was excited using common near-visible LEDs, and possesses a high triplet excited state energy of 73.3 kcal mol-1. This exactly falls in the range between the triplet energies of the enol and keto tautomer, thereby enabling a dynamic kinetic sensitization. Demonstrating the applicability of fac-[Ir(CF3-pmb)3] as a photocatalyst in organic synthesis for the first time, a two-step photocycloaddition-ring-opening cascade with β-ketoesters, -diketones, and -ketoamides was described. The mechanism was corroborated by time-resolved spectroscopy, as well as further exptl. and computational studies. The experimental process involved the reaction of Methyl 2-cyclopentanonecarboxylate(cas: 10472-24-9).Application In Synthesis of Methyl 2-cyclopentanonecarboxylate
The Article related to alkene cyclic dicarbonyl compound photocatalyst diastereoselective regioselective ring enlargement, dicarbonyl compound preparation, de mayo reaction, energy transfer, photochemistry, ring expansion, spectroscopy and other aspects.Application In Synthesis of Methyl 2-cyclopentanonecarboxylate
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