Gold-catalysed cyclic ether formation from diols

X Jiang, EK London, DJ Morris, GJ Clarkson, M Wills

Index: Jiang, Xiaolu; London, Emma K.; Morris, David J.; Clarkson, Guy J.; Wills, Martin Tetrahedron, 2010 , vol. 66, # 52 p. 9828 - 9834

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Citation Number: 16

Abstract

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 ...