title: A practical way to synthesize chiral fluoro-containing polyhydro-2H-chromenes from monoterpenoids.
abstract: Conditions enabling the single-step preparative synthesis of chiral 4-fluoropolyhydro-2H-chromenes in good yields through a reaction between monoterpenoid alcohols with para-menthane skeleton and aldehydes were developed for the first time. The BF3·Et2O/H2O system is used both as a catalyst and as a fluorine source. The reaction can involve aliphatic aldehydes as well as aromatic aldehydes containing various acceptor and donor substituents. 4-Hydroxyhexahydro-2H-chromenes were demonstrated to be capable of converting to 4-fluorohexahydro-2H-chromenes under the developed conditions, the reaction occurs with inversion of configuration.
authors.affiliation: 1N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Science, Lavrentiev ave., 9, 630090 Novosibirsk, Russian Federation.
authors.forename: Oksana S
authors.initials: OS
authors.lastname: Mikhalchenko
authors.affiliation: 1N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Science, Lavrentiev ave., 9, 630090 Novosibirsk, Russian Federation.
authors.forename: Dina V
authors.initials: DV
authors.lastname: Korchagina
authors.affiliation: 1N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Science, Lavrentiev ave., 9, 630090 Novosibirsk, Russian Federation; Novosibirsk State University, Pirogova 2, 630090 Novosibirsk, Russian Federation.
authors.forename: Konstantin P
authors.initials: KP
authors.lastname: Volcho
authors.affiliation: 1N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Science, Lavrentiev ave., 9, 630090 Novosibirsk, Russian Federation; Novosibirsk State University, Pirogova 2, 630090 Novosibirsk, Russian Federation.
authors.forename: Nariman F
authors.initials: NF
authors.lastname: Salakhutdinov
keywords: chirality; fluorine; halo-Prins reaction; isopulegol; monoterpene