FURTHER OBSERVATIONS ON THE LEWIS ACID-CATALYZED BENZYLIC HYDROPEROXIDE REARRANGEMENT: USE OF A BORON-TRIFLUORIDE/HYDROGEN PEROXIDE PREFORMED, AGED REAGENT

Article abstract of DOI:10.1016/S0040-4039(00)95902-1

A preformed, aged reagent derived from boron trifluoride etherate and 90percent hydrogen peroxide (2:1-4:1 complex) has been found to be a useful reagent for promoting the benzylic hydroperoxide rearrangement of readily oxidizable substrates bearing a free, basic amine.The use of this procedure for introduction of the C-4 phenol of the C-4/C-5 selectively-protected o-catechol unit found in PDE-I and PDE-II, naturally-occuring phosphodiesterase inhibitors constituting the central and right-hand segments of the antitumor-antibiotic CC-1065, is detailed.