Nucleophilic additions to tricyclodecadienone epoxides. The Payne rearrangement of α,β-epoxycyclopentanols contained in a rigid tricyclic system

Article abstract of DOI:10.1016/S0040-4020(01)87027-7

Organometallic reagents add regio- and stereoselectively from the convex exo-face to the carbonyl function of exo-4,5-epoxytricyclodecenones 5 and 8 to give tricyclic exo-epoxy-endo-alcohols 6 and 9, respectively. These initial adducts can undergo a Payne