Promontorio, R.; Richard, J. A.; Marson, C. M., Late-stage fluorination of bridged scaffolds : chemoselective generation of a CHF group at three positions of the bicyclo[3.3.1]nonane system. Tetrahedron Letters 2018, 59 (13), 1226-1229.
Abstract:
Monofluorobicyclo[3.3.1]nonane derivatives were prepared by late-stage fluorination, often proceeding with control of stereochemistry. Introduction of fluorine at the 3-, 6- or 7-position was achieved chemoselectively, the bicyclo system being constructed by a tandem one-pot Michael-aldol annulation. The major conformer was deduced for each of the fluorobicyclo compounds prepared, each possessing a unique CF orientation on a common rigid bridged scaffold that can be polysubstituted.
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Funding Info:
This work was funded by a studentship (to R. P.) from the EPSRC Centre for Doctoral Training in Molecular Modeling & Materials Science, University College London and from the A*STAR Graduate
Academy (A⁄GA), Singapore.