Organocatalyzed enantio- and diastereoselective isomerization of prochiral 1,3-cyclohexanediones into nonalactones bearing distant stereocenters† † Electronic supplementary information (ESI) available. CCDC 2162117. For ESI and crystallographic data in CIF or other electronic format see DOI: https://doi.org/10.1039/d2sc06842g

ABSTRACT: 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. Nine- and ten-membered lactones with up to three non-vicinal stereocenters (up to 99 : 1 er and dr) were prepared by ring expansion of prochiral alcohols (21 examples) upon exposure to quinidine and derivatives.

SUBMITTER: d’Aleman A 

PROVIDER: S-EPMC9945243 | biostudies-literature | 2023 Jan

REPOSITORIES: biostudies-literature