Organocatalyzed enantio- and diastereoselective isomerization of prochiral 1,3-cyclohexanediones into nonalactones bearing distant stereocenters - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Chemical Science Année : 2023

Organocatalyzed enantio- and diastereoselective isomerization of prochiral 1,3-cyclohexanediones into nonalactones bearing distant stereocenters

Résumé

The lactonization of 2-(2-nitrophenyl)-1,3-cyclohexanediones containing an alcohol side chain and up to three distant prochiral elements is reported by isomerization under the mediation of simple organocatalysts such as quinidine. Through a process of ring expansion, strained nonalactones and decalactone are produced with up to three stereocenters in high er and dr (up to 99 : 1). Distant groups, including alkyl, aryl, carboxylate and carboxamide moieties, were examined

Domaines

Chimie organique
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Dates et versions

hal-04256816 , version 1 (07-11-2023)

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Antoine D’aleman, Oscar Gayraud, Catherine Fressigné, Emilie Petit, Laetitia Bailly, et al.. Organocatalyzed enantio- and diastereoselective isomerization of prochiral 1,3-cyclohexanediones into nonalactones bearing distant stereocenters. Chemical Science, 2023, 14 (8), pp.2107-2113. ⟨10.1039/D2SC06842G⟩. ⟨hal-04256816⟩
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