78018-58-3Relevant articles and documents
SYNTHETIC APPLICATIONS OF CHROMIUM(VI) REAGENTS IN COMBINATION WITH CHLOROTRIMETHYLSILANE
Cossio, Fernando P.,Aizpurua, Jesus M.,Palomo, Claudio
, p. 225 - 231 (2007/10/02)
The synthetic utility of chromium(VI) reagents together with chlorotrimethylsilane, as new oxidizing systems, is described.Pyridinium dichromate (PDC) in combination with chlorotrimethylsilane oxidizes tert-butyldimethylsilyl ethers in good to excellent yields.Trimethylsilyl chlorochromate, a new chromium(VI) reagent, also was found efficient for this oxidative-deprotection method.These reagents were applied to the oxidation of some N-(2-phenyl-2-hydroxyethyl)azetidin-2-ones as well as N-(2-phenyl-2-trialkylsiloxy)azetidin-2-ones into their corresponding carbonyl compounds, key intermediates for N-unsubstituted β-lactams.Oxidation of hydroquinones and protected trialkylsilyl hydroquinones was also described.Protection of hydroquinones by means of the tert-butyldimethylsilyl group was achieved by using the readily available tert-butyldimethylchlorosilane (TBDMCS) and 1,8-diazabicycloundec-7-ene (DBU) as base, which avoids the use of sophisticated and (or) sensitive reagents.