Selective, Convenient and Efficient Deprotection of Trimethylsilyl and Tetrahydropyranyl Ethers, Ethylene Acetals and Ketals with Oxone under Non-aqueous Conditions
An efficient and selective method for the deprotection of trimethylsilyl (TMS) and tetrahydropyranyl (THP) ethers, ethylene acetals and ketals to their corresponding alcohols and carbonyl compounds using oxone in refluxing acetonitrile is described. Excellent chemoselectivity of this method makes it a useful and practical procedure in organic synthesis.
AN EFFICIENT METHOD FOR SELECTIVE DEPROTECTION OF TRIMETHYLSILYL ETHERS, TETRAHYDROPYRANYL ETHERS, ETHYLENE ACETALS, AND KETALS UNDER MICROWAVE IRRADIATION
作者:A. R. Hajipour、S. E. Mallakpour、I. Mohammadpoor-Baltork、S. Khoee
DOI:10.1081/scc-120002408
日期:2002.1.1
[2.2.2]octane dichromate (BAABOD) is a useful reagent for the selective cleavage of trimethylsilyl ethers, tetrahydropyranyl ethers, ethylene acetals and ketals to their corresponding alcohols, aldehydes and ketones. This method is very simple and efficient and the reaction has been carried out under microwave irradiation.
The synthetic utility of potassium dichromate in the presence of Lewis acids under solid phase conditions is described. This reagent efficiently oxidizes alcohols, acyloins, oximes and semicarbazones to their corresponding carbonyl compounds, while trimethylsilyl and tetrahydropyranylethers, ethylene acetals and ketals undergo oxidative deprotection to produce carbonyl compounds efficiently.
OXIDATIVE DEPROTECTION OF TRIMETHYLSILYL ETHERS, TETRAHYDROPYRANYL ETHERS, AND ETHYLENE ACETALS WITH BENZYLTRIPHENYLPHOSPHONIUM PEROXYMONOSULFATE UNDER MICROWAVE IRRADIATION
作者:A. R. Hajipour、S. E. Mallakpour、I. M. Baltork、H. Adibi
DOI:10.1081/scc-100103980
日期:2001.1
This paper describes the oxidation deprotection of trimethylsilyl ethers, tetrahydrophyranyl ethers and deprotection of ethylene acetals to afford carbonyl compounds using benzyltriphenylphosphonium peroxymonosulfate (1) (PhCH2PPh3HSO5) in the presence of a catalytic amount of bismuth chloride under microwave irradiation. This reagent is a stable white powder, which has been prepared by the dropwise
AN EASY AND FAST METHOD FOR OXIDATIVE DEPROTECTION OF TRIMETHYLSILYL ETHERS, TETRAHYDROPYRANYL ETHERS, AND ETHYLENE ACETALS WITH KMnO<sub>4</sub> SUPPORTED ON ALUMINA UNDER SOLVENT-FREE CONDITIONS
作者:A. R. Hajipour、S E. Mallakpour、I. M. Baltork、H. Backnezhad
DOI:10.1081/scc-120002518
日期:2002.1.1
ABSTRACT A manipulatively simple and rapid method for oxidation deprotection of trimethylsilylethers, tetrahydropyranyl ethers and deprotection of ethylene acetals to afford carbonyl compounds undersolvent-freeconditions in the presence or absence of alumina with potassium permanganate.