Beilstein J. Org. Chem.2016,12, 648–653, doi:10.3762/bjoc.12.64
was 7% (Table 2). Thus, we found for the first time the conditions enabling production of chiral fluoro-containing heterocyclic compounds from a monoterpenoid using the halo-Prinscyclisation.
It should also be noted that preparative isolation of compounds of type 7a is complicated by the presence of
as fluorine sources.
Presumably, the reaction starts with the Prinscyclisation resulting in the formation of cation 10. There are then several mechanistic pathways, some or all of them may be in operation: a) cation 10 may undergo stereoselective trap by [F−] to form fluoride epimers 8; b) cation 10
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Graphical Abstract
Scheme 1:
Reaction between monoterpenoid 1 and aromatic aldehydes in the presence of K10 montmorillonite clay....
Beilstein J. Org. Chem.2010,6, No. 41, doi:10.3762/bjoc.6.41
.
Keywords: 4-fluoropiperidine; 4-fluoropyran; heterocycles; organo-fluorine chemistry; Prinscyclisation; Introduction
Selective incorporation of the C–F bond into organic molecules can impart useful and attractive properties to performance materials [1][2][3]. To this end there are a useful but relatively
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Graphical Abstract
Scheme 1:
The C–F bond forming Prins reaction leading to 4-fluoropyrans [10].