Prins cyclization of α-bromoethers under basic conditions

P Arpin, B Hill, R Larouche-Gauthier…

Index: Arpin, Patrice; Hill, Bryan; Larouche-Gauthier, Robin; Spino, Claude Canadian Journal of Chemistry, 2013 , vol. 91, # 12 p. 1193 - 1201

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Abstract

α-Bromoethers have been found to undergo Prins-type cyclization under basic conditions and without the need to add a promoter. The products are those derived from a Markovnikov addition on the pendant alkene. However, the stereochemistry and even the structure of the products sometimes differ from those expected with the classical Lewis-acid-catalyzed Prins reaction of acetals.