title: The Prins reaction using ketones: rationalization and application toward the synthesis of the portentol skeleton.
abstract: We report a TMSI-promoted Prins cyclization reaction with ketones as carbonyl partners to prepare polysubstituted chiral spirotetrahydropyrans. In the presence of racemic 2-methylcyclohexanone a dynamic kinetic resolution occurred affording one stereoisomer. The observed enantiospecificity has been rationalized by DFT calculation.
authors: Université de Rennes 1, UMR 6226, Sciences Chimiques de Rennes, Equipe PNSCM, UFR des Sciences Biologiques et Pharmaceutiques, 2 avenue du Prof Léon Bernard, F-35043 Rennes Cedex, France.
authors: Maiwenn
authors: M
authors: Jacolot
authors: Mickael
authors: M
authors: Jean
authors: Nicolas
authors: N
authors: Levoin
authors: Pierre
authors: P
authors: van de Weghe
mesh_terms: D003500:Cyclization; D007659:Ketones / Q000737:chemistry*; D007700:Kinetics; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis*; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D007659:Ketones; D011714:Pyrans; D013141:Spiro Compounds; C571246:portentol