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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.
Highlights
All moisture-sensitive reactions were performed under an atmosphere of argon
using glassware pre-dried in an oven
Thin-layer chromatography was performed on Merck 0.2 mm aluminium-backed silica gel 60 F254 plates
Summary
All moisture-sensitive reactions were performed under an atmosphere of argon and using glassware pre-dried in an oven (100 °C). Thin-layer chromatography was performed on Merck 0.2 mm aluminium-backed silica gel 60 F254 plates and visualised by UV (254 nm) or by staining with potassium permanganate with subsequent heating. Flash column chromatography was performed using Merck 0.040-0.063 mm, 230-400 mesh silica gel. Infrared (IR) spectra were recorded on a Perkin-Elmer Spectrum One FT-IR spectrometer; absorptions are quoted in wavenumbers. 1H and 3C NMR spectra were recorded on a Bruker DRX-400 (400 MHz) spectrometer and calibrated using residual undeuterated solvent as an internal reference; chemical shifts are in parts per million ( ) and coupling constants (J) are given in Hertz (Hz). The following abbreviations were used in signal assignments: singlet (s), broad singlet (br s), doublet (d), triplet (t), quartet (q), and multiplet (m). Equivocal assignments are denoted by an asterisk. High-resolution mass spectra (HRMS) were obtained using either an Agilent ESI-TOF (time of flight) mass spectrometer at 3500 V emitter voltage, or using a VG7070H mass spectrometer with Finigan Incos II data system at University College London
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