261376-68-5Relevant academic research and scientific papers
Vanadium(III) chloride (VCl3): Efficient reagent for the introduction of tetrahydrofuran-based acetal protecting groups for alcohols
Das, Biswanath,Krishnaiah, Maddeboina,Reddy, Vtukuri Saidi,Laxminarayana, Keetha
, p. 2163 - 2166 (2008/03/18)
Treatment of different types of alcohols with tetrahydrofuran (THF) in the presence of VCl3 and CCl4 smoothly afforded the corresponding THF-based acetals in excellent yields. The reaction is fast at room temperature, and several functional groups are tolerated, with no racemization being observed. A radical mechanism, based on Cl3C ? as the active species, is proposed for this novel kind of transformation, which complements the classical tetrahydro-2H-pyran-2-yl (THP) protocol.
Use of allyl, 2-tetrahydrofuryl, and 2-tetrahydropyranyl ethers as useful C3-, C4-, and C5-carbon sources: Palladium-catalyzed allylation of aldehydes
Shimizu, Masamichi,Kimura, Masanari,Tamaru, Yoshinao
, p. 6629 - 6642 (2007/10/03)
Palladium-diethylzinc or palladium-triethylborane catalytically promotes self-allylation of 2-(allyloxy)tetrahydrofurans, 2-(allyloxy)tetrahydropyrans, and their hydroxy derivatives on the rings (ribose, glucose, mannose, deoxyribose, deoxyglucose). All the reactions proceed at room temperature and provide polyhydroxyl products, sharing a structural motif of a homoallyl alcohol, in good to excellent yields with high levels of stereoselectivity. Useful Crunit elongation, which makes the best use of an allyl ether as a protecting group and a nucleophilic allylation agent, is demonstrated. Mechanisms for the umpolung reaction (of an allyl ether into an allylic anion) and stereoselectivity associated with allylation of aldehydes are discussed.
Pd-catalyzed nucleophilic alkylation of aliphatic aldehydes with allyl alcohols: Allyl, 2-tetrahydrofuryl, and 2-tetrahydropyranyl ethers as useful C3, C4, and C5 sources
Kimura, Masanari,Shimizu, Masamichi,Shibata, Kazufumi,Tazoe, Minoru,Tamaru, Yoshinao
, p. 3392 - 3395 (2007/10/03)
A combination of Pd° and Et2Zn generates an allyl anion species from allyl alcohols which can be used for the allylation of aliphatic aldehydes to provide homoallyl alcohols in good yields (see scheme). The reaction proceeds at room temperature in poor coordination solvents, such as a mixture of toluene and n-hexane.
An efficient and extremely mild method for protecting alcohols as 2-tetrahydrofuranyl ethers
Barks,Gilbert,Parsons,Upeandran
, p. 6249 - 6252 (2007/10/03)
Reaction of primary or secondary alcohols with BrCCl3 and tetrahydrofuran, usually in the presence of 2,4,6-collidine, leads to the formation of 2-tetrahydrofuranyl ethers in good to excellent yield (56-92%). The reaction mechanism is believed to involve a free-radical chain reaction. (C) 2000 Elsevier Science Ltd.
