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
2000
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.
Show more [+] Less [-]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.
Show more [+] Less [-]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.
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