Département de chimie moléculaire

A general method to prep. a new class of carbohydrate-derived, enantiomerically pure polyhydroxypyrroline N-oxides, e.g. I, from their alkoxy (protected) derivs. is presented. Boron trichloride is shown to cleave efficiently benzyl ethers and ketals without affecting the imine N-oxide functionality of nitrones. The same reagent (BCl3) also allowed the efficient synthesis of a polyhydroxylated N-hydroxypyrrolidine II, giving access to a novel class of N-hydroxyiminosugars. [on SciFinder(R)]