Prins fluorination cyclisations : Preparation of 4-fluoro-pyran and -piperidine heterocycles
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The Prins reaction was investigated using BF3 center dot OEt2 as a Lewis acid. It has been recently demonstrated, that if BF3 center dot OEt2 is used in stoichiometric amounts then these reactions generate fluorinated products where the BF3 center dot OEt2 contributes fluoride ion to quench the intermediate carbocations. In this study oxa- and aza-Prins reactions for the synthesis of 4-fluoro-pyrans and -piperidines were investigated. The products were obtained in good yields, but only with moderate diastereoselectivity. These Prins fluorination reactions can be accelerated under microwave conditions. The study extends the Prins fluorination methodology for the generation of the C-F bond in heterocycles.
Launay , G G , Slawin , A M Z & O'Hagan , D 2010 , ' Prins fluorination cyclisations : Preparation of 4-fluoro-pyran and -piperidine heterocycles ' Beilstein Journal of Organic Chemistry , vol 6 , 41 . DOI: 10.3762/bjoc.6.41
Beilstein Journal of Organic Chemistry
© 2010 Launay et al; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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