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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.

SUBMITTER: Mikhalchenko OS

PROVIDER: S-EPMC4902074 | biostudies-literature | 2016

REPOSITORIES: biostudies-literature

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

Mikhalchenko Oksana S OS Korchagina Dina V DV Volcho Konstantin P KP Salakhutdinov Nariman F NF

Beilstein journal of organic chemistry 20160406

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 ...[more]

PMID: 27340456

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