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Control of Diastereoselectivity in C=O/C=N Reductive Cyclizations Using an Intramolecularly Tethered Hydrazone

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dc.creator Chiara, José Luis
dc.creator García, Ángela
dc.date 2007-11-12T11:26:56Z
dc.date 2007-11-12T11:26:56Z
dc.date 2005-10
dc.date.accessioned 2017-01-31T00:58:17Z
dc.date.available 2017-01-31T00:58:17Z
dc.identifier Synlett 17 (2005), pp. 2607-2610
dc.identifier http://hdl.handle.net/10261/1981
dc.identifier 10.1055/s-2005-917083
dc.identifier.uri http://dspace.mediu.edu.my:8181/xmlui/handle/10261/1981
dc.description Cyclic hydrazones are efficient ketyl radical acceptors in reductive coupling cyclizations mediated by samarium diiodide, affording cyclic amino alcohols with controlled stereochemistry at the new aminated stereocenter. This approach has been successfully applied to the stereoselective synthesis of a fully functionalized trehazolin cyclitol starting from D-glucose, where the required cyclic hydrazone was directly obtained by partial hydrazynolysis of a 1,2-cyclic carbonate.
dc.description Financial support by the Ministry of Science and Technology of Spain (project BQU2000-1501-C02-01) and Fundación Ramón Areces (predoctoral fellowship to A. G.) are gratefully acknowledged.
dc.description Peer reviewed
dc.language eng
dc.publisher Thieme
dc.rights openAccess
dc.subject Carbohydrates
dc.subject Electron transfer
dc.subject Hydrazones
dc.subject Ketones
dc.subject Samarium
dc.title Control of Diastereoselectivity in C=O/C=N Reductive Cyclizations Using an Intramolecularly Tethered Hydrazone
dc.type Artículo


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