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

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

Journal

Beilstein Journal of Organic Chemistry
ISSN: 1860-5397

Output data

Year: 2016, Volume: 12, Pages: 648-653 Pages count : 6 DOI: 10.3762/bjoc.12.64

Tags

chirality; fluorine; halo-Prins reaction; isopulegol; monoterpene

Authors

Mikhalchenko Oksana S. ¹ , Korchagina Dina V. ¹ , Volcho Konstantin P. ^1,2 , Salakhutdinov Nariman F. ^1,2

Affiliations

1	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Lavrentiev Ave 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Pirogova 2, Novosibirsk 630090, Russia

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 center dot 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.

Mikhalchenko O.S. , Korchagina D.V. , Volcho K.P. , Salakhutdinov N.F.
A practical way to synthesize chiral fluoro-containing polyhydro-2H-chromenes from monoterpenoids

Beilstein Journal of Organic Chemistry. 2016. V.12. P.648-653. DOI: 10.3762/bjoc.12.64 WOS Scopus РИНЦ

Full text from publisher

Published online:

Apr 6, 2016

Web of science	WOS:000373699500001
Scopus	2-s2.0-84976310115
Elibrary	27140678
OpenAlex	W2328793031