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Synlett 2001; 2001(12): 1989-1991
DOI: 10.1055/s-2001-18765
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Iodine in Dichloromethane - A Simple Method for Selective Cleavage of Prenyl Ethers

Jean-Michel Vatèle*
  • *Laboratoire de Chimie Organique 1, UMR 5622 CNRS, domaine scientifique de la Doua, CPE, 3 rue Victor Grignard, 69616 Villeurbanne Cedex, France; Fax: + 33(4724)31214; E-mail: vatele@univ-lyon1.fr
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Publication Date:
04 December 2001 (online)

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Treatment of prenyl (Pre) ethers of simple alcohols, carbohydrates, steroids, with I2 in CH2Cl2 in the presence of 3Å molecular sieves, constitutes an effective method for their deprotection. This method tolerates other etheral functionalities such as acetals, allyl, t-butyldiphenylsilyl or benzyl groups as well as base labile groups such as acetates. This method applied to a prenyl aryl ether gave rise to a 2,2-dimethylchroman derivative in an acceptable yield.

chromans - iodine - prenyl ethers - protecting groups