Novel polyhydroxylated cyclic nitrones and N-hydroxypyrrolidines through BCl3-mediated deprotection.
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.
Desvergnes
Stéphanie
S
Département de Chimie Moléculaire (SERCO), CNRS-Université Joseph Fourier, Grenoble Cedex, France.
Vallée
Yannick
Y
Py
Sandrine
S
D001880:Boranes / Q000737:chemistry*; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D003497:Cyclic N-Oxides / Q000138:chemical synthesis* / Q000737:chemistry; D050111:Imino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000138:chemical synthesis* / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry
D001880:Boranes; D002712:Chlorides; D003497:Cyclic N-Oxides; D050111:Imino Sugars; D009589:Nitrogen Oxides; D011759:Pyrrolidines; C015388:nitrones; C092267:boron trichloride