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http://dspace.mediu.edu.my:8181/xmlui/handle/10261/1981| Title: | Control of Diastereoselectivity in C=O/C=N Reductive Cyclizations Using an Intramolecularly Tethered Hydrazone |
| Keywords: | Carbohydrates Electron transfer Hydrazones Ketones Samarium |
| Publisher: | Thieme |
| 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. 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. Peer reviewed |
| URI: | http://dspace.mediu.edu.my:8181/xmlui/handle/10261/1981 |
| Other Identifiers: | Synlett 17 (2005), pp. 2607-2610 http://hdl.handle.net/10261/1981 10.1055/s-2005-917083 |
| Appears in Collections: | Digital Csic |
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