17912-15-1Relevant articles and documents
Iron(III)-catalyzed Prins-type cyclization using homopropargylic alcohol: A method for the synthesis of 2-alkyl-4-halo-5,6-dihydro-2H-pyrans
Miranda, Pedro O.,Diaz, David D.,Padron, Juan I.,Bermejo, Jaime,Martin, Victor S.
, p. 1979 - 1982 (2003)
(Matrix presented) A new Prins-type cyclization between homopropargylic alcohol and aldehydes in the presence of FeX3 to obtain 2-alkyl-4-halo-5,6-dihydro2H-pyrans in good yield is described. Osmium-catalyzed cis dihydroxylation provided direct
Gold-catalysed cyclic ether formation from diols
Jiang, Xiaolu,London, Emma K.,Morris, David J.,Clarkson, Guy J.,Wills, Martin
experimental part, p. 9828 - 9834 (2011/02/23)
Gold(I) and (III) salts have been found to be highly effective at the catalysis of ether formation from alcohols. Intramolecular ether formation of a 1,5-diol was also achieved, with a stereoselectivity that indicates that an SN1 mechanism predominates. In an attempt to form a seven-membered ring, a stable 14-membered dimer product was also formed. Attempts to control the diastereoselectivity of the reaction using a chiral anionic counterion did not give products with a high de.