A Mn(OAc)3 -Triggered Formation of Cyclopropanes from Ugi Adducts.

Autor: Cheibas, Cristina, Vieu, Emilie, Casaretto, Nicolas, Vitale, Maxime, Grimaud, Laurence, El Kaïm, Laurent
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Zdroj: Synlett; Aug2023, Vol. 34 Issue 13, p1581-1586, 6p
Abstrakt: [2] Following our interest in Ugi reactions and the use of the latter in radical reactions, [9] we envisioned that a variant of the intramolecular Buchner reaction could be devised using a twofold Mn(III) oxidation of malonic acid derivatives. Keywords: manganese acetate; Ugi reaction; radical cyclization; cyclopropanation EN manganese acetate Ugi reaction radical cyclization cyclopropanation 1581 1586 6 07/31/23 20230815 NES 230815 Graph Already known in the 19 SP th sp century, the Buchner ring expansion of aromatic compounds involves as key steps the ring opening of transient cyclopropanes formed under addition of carbenes onto the aromatic rings. [9] As the two cyclization steps which are required to reach the expected Buchner-type cyclopropanes entail a global 4-electron oxidation, at least 4 equiv of Mn(OAc) SB 3 sb had to be used. [Extracted from the article]
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