The coupling reaction of a D-ribofuranosyl fluoride with indoles in the presence of boron trifluoride gives the corresponding C-nucleosides in a stereoselective manner depending upon reaction temperatures and solvents: the β-anomer is preferred under such conditions as –15 to –40 °C in nitroethane while the α-anomer is preferred at –78 °C in propiononitrile.
M. Yokoyama, M. Nomura, H. Togo and H. Seki, J. Chem. Soc., Perkin Trans. 1, 1996, 2145 DOI: 10.1039/P19960002145
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