期刊
TETRAHEDRON LETTERS
卷 59, 期 13, 页码 1226-1229出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2018.02.038
关键词
Tandem Michael-aldol addition; Fluorobicyclo[3.3.1]nonanes; Chemoselective fluorination; DFT calculations; alpha-fluoroketone conformers
资金
- EPSRC Centre for Doctoral Training in Molecular Modeling & Materials Science, University College London
- A*STAR Graduate Academy (A*GA), Singapore
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 C-F orientation on a common rigid bridged scaffold that can be polysubstituted. (C) 2018 The Authors. Published by Elsevier Ltd.
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