Abstract
Triflic acid catalyzed cascade stereoselective reaction of glycals with styrenes delivers complex oxabicyclic scaffolds such as cis-oxadecalins or cis-cyclopentanofurans simply by tweaking the solvent. In the presence of participating solvents like benzene/toluene, cascade Ferrier C-glycosylation and double Friedel-Crafts reaction leads to densely chiral benzo-fused oxadecalins, whereas in DCM, an unprecedented ring-opening, ring-closing sequence generated cis-cyclopentanofurans. An attempt has been made to explain the above cascade sequences via intermediate trapping, kinetic experiments, and Baldwin's rules.
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