volume 30, issue 43, Pno-no 2010
DOI: 10.1002/chin.199943158
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Jennifer E. Forsee,
Jeffrey Aube

Abstract: Hydrolysis of Iminium Ethers Derived from the Reaction of Ketones with Hydroxy Azides: Synthesis of Macrocyclic Lactams and Lactones.-It is shown that the reaction of azido alcohols (II) or (V) with cyclic ketones containing 7-to 12-membered rings affords lactams or lactones whose relative amounts depend mainly on the structures of the reactants and the pH of the basic media used to hydrolyze the iminium ether intermediates. A mechanism is suggested. The results are similar to those obtained earlier with cycl…

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