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A practical way to synthesize chiral fluoro-containing polyhydro-2H-chromenes from monoterpenoids

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 BF(3)·Et(2)O/H(2)O system is used both as a catalyst an...

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Detalles Bibliográficos
Autores principales: Mikhalchenko, Oksana S, Korchagina, Dina V, Volcho, Konstantin P, Salakhutdinov, Nariman F
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4902074/
https://www.ncbi.nlm.nih.gov/pubmed/27340456
http://dx.doi.org/10.3762/bjoc.12.64
Descripción
Sumario: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 BF(3)·Et(2)O/H(2)O 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.