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Synthesis of Aminocyclitols by Intramolecular Reductive Coupling of Carbohydrate Derived δ- and ε-Functionalized Oxime Ethers Promoted by Tributyltin Hydride or Samarium Diiodide

AuthorsMarco-Contelles, José ; Gallego, Pilar; Rodríguez-Fernández, Mercedes; Khiar el Wahabi, Noureddine ; Destabel, Christine; Bernabé, Manuel ; Martínez-Grau, Angeles; Chiara, José Luis
Issue Date17-Oct-1997
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 62(21): 7397-7412 (1997)
AbstractThe intramolecular reductive coupling of a series of simple or polyoxygenated oxime ethers δ- or ε-functionalized with bromide, α,β-unsaturated ester, aldehyde, or ketone groups is reported. The cyclization of a nitrile-tethered aldehyde is also studied. These reductive couplings are promoted by tributyltin hydride or samarium diiodide. The reactions proceed under mild conditions, in good chemical yield, and with high stereoselectivity. When applied to highly functionalized substrates derived from carbohydrates, this approach provides a selective entry to enantiomerically pure aminocyclitols of varying regio- and stereochemistry. In particular, the reductive coupling reaction of carbonyl-tethered oxime ethers promoted by samarium diiodide can be performed in a one-pot sequence, following a Swern oxidation step, allowing the direct transformation of hydroxyl-tethered oxime ethers into the corresponding aminocyclitols. Moreover, the resultant O-benzylhydroxylamine products of these cyclizations can be further reduced in situ with excess samarium diiodide, in the presence of water, to the corresponding amino alcohols in excellent yields. Some transformations of these compounds are discussed.
Description16 páginas, 2 figuras, 18 esquemas, 1 tabla.-- Supporting Information Available: Experimental procedures and characterization data for compounds 7b-e, 23, 54, and 56, and tables of 1H NMR and 2D NOESY cross-peak intensities for the carbocyclic products 39, 43, 44a-c, 45, 50ad, 51a,b, 52a,b, 65a-c (8 pages).
Publisher version (URL)http://dx.doi.org/10.1021/jo970987w
Appears in Collections:(IQOG) Artículos
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