57713-26-5Relevant academic research and scientific papers
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 (2005)
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.
Efficient and ecofriendly protocol for tetrahydropyranylation/ depyranylation of alcohols in the presence of tin(II) chloride dihydrate
Gogoi, Dipankoj,Baruah, Nabajyoti,Bez, Ghanashyam
, p. 595 - 599 (2007/10/03)
A mild, efficient, and solvent-free protocol for tetrahydropyranylation of alcohols in the presence of a catalytic amount of SnCl2·2H2O is reported. Simple filtration of the reaction mixture through a short silica-gel pad gives the pure products in excellent yields. Depyranylation can also be achieved by adding methanol under similar reaction conditions. Copyright Taylor & Francis Group, LLC.
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.
