Rossella Promontorio, Jean-Alexandre Richard, Charles M. Marson, 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, Volume 59, Issue 13, 2018, Pages 1226-1229, ISSN 0040-4039, https://doi.org/10.1016/j.tetlet.2018.02.038.
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.
License type:
http://creativecommons.org/licenses/by/4.0/
Funding Info:
Financial support for 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 is gratefully acknowledged.