The stereospecific condensation of vinylmagnesium bromide with the readily available aldehyde 2, gave the olefin 3 which was further elaborated into L-glycerol-D-manno-heptose and some derivatives thereof, through oxidative cleavage of the double bond followed by reductive work up.
M. Dasser, F. Chrétien and Y. Chapleur, J. Chem. Soc., Perkin Trans. 1, 1990, 3091 DOI: 10.1039/P19900003091
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