Synthetic applications of chromium(VI) reagents in combination with chlorotrimethylsilane

1 February 1986

journal article
Published by Canadian Science Publishing in Canadian Journal of Chemistry

Vol. 64 (2) , 225-231
https://doi.org/10.1139/v86-039

Abstract

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-diazabicyclo[5.4.0]undec-7-ene (DBU) as base, which avoids the use of sophisticated and (or) sensitive reagents.

Keywords

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