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Hypervalent Iodine
Molecules 2005, 10(1), 183-189; doi:10.3390/10010183
Article

Stereoselective Synthesis of 5-7 membered Cyclic Ethers by Deiodonative Ring-Enlargement Using Hypervalent Iodine Reagents

, ,  and *
Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan
* Author to whom correspondence should be addressed.
Received: 19 April 2004 / Revised: 15 January 1995 / Accepted: 1 July 2004 / Published: 31 January 2005
(This article belongs to the Special Issue Hypervalent Iodine)
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Abstract

Stereoselective synthesis of 5-7 membered cyclic ethers was achieved by deiodonative ring-enlargement of cyclic ethers having an iodoalkyl substituent. The reaction took place readily under mild conditions using hypervalent iodine compounds and an acetoxy or a trifluoroacetoxy group was introduced into the rings depending on the hypervalent iodine reagent employed. The use of hexafluoroisopropanol (HFIP) as solvent is critical.
Keywords: Ring-enlargement; cyclic ether; hypervalent iodine compounds. Ring-enlargement; cyclic ether; hypervalent iodine compounds.
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Abo, T.; Sawaguchi, M.; Senboku, H.; Hara, S. Stereoselective Synthesis of 5-7 membered Cyclic Ethers by Deiodonative Ring-Enlargement Using Hypervalent Iodine Reagents. Molecules 2005, 10, 183-189.

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