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

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 i...

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Autores principales: Abo, Tomohito, Sawaguchi, Masanori, Senboku, Hisanori, Hara, Shoji
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2005
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6147675/
https://www.ncbi.nlm.nih.gov/pubmed/18007285
http://dx.doi.org/10.3390/10010183
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author Abo, Tomohito
Sawaguchi, Masanori
Senboku, Hisanori
Hara, Shoji
author_facet Abo, Tomohito
Sawaguchi, Masanori
Senboku, Hisanori
Hara, Shoji
author_sort Abo, Tomohito
collection PubMed
description 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.
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spelling pubmed-61476752018-11-19 Stereoselective Synthesis of 5-7 membered Cyclic Ethers by Deiodonative Ring-Enlargement Using Hypervalent Iodine Reagents Abo, Tomohito Sawaguchi, Masanori Senboku, Hisanori Hara, Shoji Molecules Article 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. MDPI 2005-01-31 /pmc/articles/PMC6147675/ /pubmed/18007285 http://dx.doi.org/10.3390/10010183 Text en © 2005 by MDPI (http:www.mdpi.org). Reproduction is permitted for noncommercial purposes.
spellingShingle Article
Abo, Tomohito
Sawaguchi, Masanori
Senboku, Hisanori
Hara, Shoji
Stereoselective Synthesis of 5-7 membered Cyclic Ethers by Deiodonative Ring-Enlargement Using Hypervalent Iodine Reagents
title Stereoselective Synthesis of 5-7 membered Cyclic Ethers by Deiodonative Ring-Enlargement Using Hypervalent Iodine Reagents
title_full Stereoselective Synthesis of 5-7 membered Cyclic Ethers by Deiodonative Ring-Enlargement Using Hypervalent Iodine Reagents
title_fullStr Stereoselective Synthesis of 5-7 membered Cyclic Ethers by Deiodonative Ring-Enlargement Using Hypervalent Iodine Reagents
title_full_unstemmed Stereoselective Synthesis of 5-7 membered Cyclic Ethers by Deiodonative Ring-Enlargement Using Hypervalent Iodine Reagents
title_short Stereoselective Synthesis of 5-7 membered Cyclic Ethers by Deiodonative Ring-Enlargement Using Hypervalent Iodine Reagents
title_sort stereoselective synthesis of 5-7 membered cyclic ethers by deiodonative ring-enlargement using hypervalent iodine reagents
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6147675/
https://www.ncbi.nlm.nih.gov/pubmed/18007285
http://dx.doi.org/10.3390/10010183
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AT senbokuhisanori stereoselectivesynthesisof57memberedcyclicethersbydeiodonativeringenlargementusinghypervalentiodinereagents
AT harashoji stereoselectivesynthesisof57memberedcyclicethersbydeiodonativeringenlargementusinghypervalentiodinereagents

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