Ps. Aburel et al., Synthesis of alpha-hydroxy and alpha-oxospiranes through ruthenium(II)-catalyzed ring-closing metathesis, J CHEM S P1, (12), 2001, pp. 1458-1472
Efficient methodology for the construction of functionalized spiranes using
Ru(II)-catalyzed ring-closing metathesis reactions is described. The subst
rates were appropriately substituted five-, six- and seven-membered cycloal
kanes which were spiroannulated by five-, six- and seven-membered rings, re
spectively. The relative stereochemistry of selected substituted spiranes h
as been determined by single crystal X-ray analyses. The X-ray structures f
ormed the basis for NMR correlations of the relative stereochemistry in the
groups of compounds prepared. Relative rates in oxidation reactions could
also be used for stereochemical correlations.