- Novel polyhydroxylated cyclic nitrones and N-hydroxypyrrolidines through BCl3-mediated deprotection.
Novel polyhydroxylated cyclic nitrones and N-hydroxypyrrolidines through BCl3-mediated deprotection.
Organic letters (2008-06-24)
Stéphanie Desvergnes, Yannick Vallée, Sandrine Py
PMID18570375
ABSTRACT
A general method to prepare a new class of carbohydrate-derived, enantiomerically pure polyhydroxypyrroline N-oxides from their alkoxy (protected) derivatives 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, giving access to a novel class of N-hydroxyiminosugars.
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