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

doi:10.3390/10010183

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

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

Tomohito Abo, Masanori Sawaguchi, Hisanori Senboku and Shoji Hara*

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; in revised form: 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.

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MDPI and ACS Style

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.

AMA Style

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(1):183-189.

Chicago/Turabian Style

Abo, Tomohito; Sawaguchi, Masanori; Senboku, Hisanori; Hara, Shoji. 2005. "Stereoselective Synthesis of 5-7 membered Cyclic Ethers by Deiodonative Ring-Enlargement Using Hypervalent Iodine Reagents." Molecules 10, no. 1: 183-189.

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