Intramolecular hydrogen abstraction reaction in carbohydrate chemistry. Synthesis of chiral 2,7-dioxabicyclo[2.2.1]heptane and 6,8-dioxabicyclo[3.2.1]octane ring systems

Intramolecular hydrogen abstraction reaction in carbohydrate chemistry. Synthesis of chiral 2,7-dioxabicyclo[2.2.1]heptane and 6,8-dioxabicyclo[3.2.1]octane ring systems

5 pages, 1 table, 1 scheme.

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Bibliographic Details
Main Authors: Francisco, Cosme G., Herrera, Antonio J., Suárez, Ernesto
Other Authors: Dirección General de Investigación Científica y Técnica, DGICT (España)
Format: artículo biblioteca
Language:English
Published: Elsevier 2000-10-07
Online Access:http://hdl.handle.net/10261/17233
http://dx.doi.org/10.13039/501100008737
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spelling dig-ipna-es-10261-172332019-11-13T08:48:56Z Intramolecular hydrogen abstraction reaction in carbohydrate chemistry. Synthesis of chiral 2,7-dioxabicyclo[2.2.1]heptane and 6,8-dioxabicyclo[3.2.1]octane ring systems Francisco, Cosme G. Herrera, Antonio J. Suárez, Ernesto Dirección General de Investigación Científica y Técnica, DGICT (España) Ministerio de Educación y Ciencia (España) 5 pages, 1 table, 1 scheme. The reaction of specifically protected alditols with (diacetoxyiodo)benzene or iodosylbenzene and iodine is a mild and selective procedure for the synthesis of chiral 6,8-dioxabicyclo[3.2.1]octane and 2,7-dioxabicyclo[2.2.1]heptane ring systems under neutral conditions. This methodology can be useful not only for the preparation of chiral synthons but also for the selective oxidation of specific carbons of the carbohydrate skeleton, constituting a good procedure for the synthesis of protected uloses. This reaction could be considered to be an intramolecular glycosidation that proceeds through an oxycarbenium ion. This work was supported by Investigation Programme PB96-1461 of the Dirección General de Investigación Científica y Técnica. A.J.H. thanks the Ministerio de Education y Ciencia, Spain, for a fellowship. 2009-09-29T07:47:28Z 2009-09-29T07:47:28Z 2000-10-07 artículo http://purl.org/coar/resource_type/c_6501 Tetrahedron Letters 41(41): 7869-7873 (2000) 0040-4039 http://hdl.handle.net/10261/17233 10.1016/S0040-4039(00)01393-9 http://dx.doi.org/10.13039/501100008737 en http://dx.doi.org/10.1016/S0040-4039(00)01393-9 none 2373 bytes 509639 bytes text/plain application/pdf Elsevier
institution IPNA ES
collection DSpace
country España
countrycode ES
component Bibliográfico
access En linea
databasecode dig-ipna-es
tag biblioteca
region Europa del Sur
libraryname Biblioteca del IPNA España
language English
description 5 pages, 1 table, 1 scheme.
author2 Dirección General de Investigación Científica y Técnica, DGICT (España)
author_facet Dirección General de Investigación Científica y Técnica, DGICT (España)
Francisco, Cosme G.
Herrera, Antonio J.
Suárez, Ernesto
format artículo
author Francisco, Cosme G.
Herrera, Antonio J.
Suárez, Ernesto
spellingShingle Francisco, Cosme G.
Herrera, Antonio J.
Suárez, Ernesto
Intramolecular hydrogen abstraction reaction in carbohydrate chemistry. Synthesis of chiral 2,7-dioxabicyclo[2.2.1]heptane and 6,8-dioxabicyclo[3.2.1]octane ring systems
author_sort Francisco, Cosme G.
title Intramolecular hydrogen abstraction reaction in carbohydrate chemistry. Synthesis of chiral 2,7-dioxabicyclo[2.2.1]heptane and 6,8-dioxabicyclo[3.2.1]octane ring systems
title_short Intramolecular hydrogen abstraction reaction in carbohydrate chemistry. Synthesis of chiral 2,7-dioxabicyclo[2.2.1]heptane and 6,8-dioxabicyclo[3.2.1]octane ring systems
title_full Intramolecular hydrogen abstraction reaction in carbohydrate chemistry. Synthesis of chiral 2,7-dioxabicyclo[2.2.1]heptane and 6,8-dioxabicyclo[3.2.1]octane ring systems
title_fullStr Intramolecular hydrogen abstraction reaction in carbohydrate chemistry. Synthesis of chiral 2,7-dioxabicyclo[2.2.1]heptane and 6,8-dioxabicyclo[3.2.1]octane ring systems
title_full_unstemmed Intramolecular hydrogen abstraction reaction in carbohydrate chemistry. Synthesis of chiral 2,7-dioxabicyclo[2.2.1]heptane and 6,8-dioxabicyclo[3.2.1]octane ring systems
title_sort intramolecular hydrogen abstraction reaction in carbohydrate chemistry. synthesis of chiral 2,7-dioxabicyclo[2.2.1]heptane and 6,8-dioxabicyclo[3.2.1]octane ring systems
publisher Elsevier
publishDate 2000-10-07
url http://hdl.handle.net/10261/17233
http://dx.doi.org/10.13039/501100008737
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AT herreraantonioj intramolecularhydrogenabstractionreactionincarbohydratechemistrysynthesisofchiral27dioxabicyclo221heptaneand68dioxabicyclo321octaneringsystems
AT suarezernesto intramolecularhydrogenabstractionreactionincarbohydratechemistrysynthesisofchiral27dioxabicyclo221heptaneand68dioxabicyclo321octaneringsystems
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