171877-85-3Relevant academic research and scientific papers
Synthesis of aminocyclitols by intramolecular reductive coupling of carbohydrate derived δ- and ε-functionalized oxime ethers promoted by tributyltin hydride or samarium diiodide
Marco-Contelles, Jose,Gallego, Pilar,Rodriguez-Fernandez, Mercedes,Khiar, Noureddine,Destabel, Christine,Bernabe, Manuel,Martinez-Grau, Angeles,Chiara, Jose Luis
, p. 7397 - 7412 (1997)
The 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.
A Novel and Concise Synthesis of Aminocyclopentitols and 1-Deoxynojirimycin via Radical Cyclization of Oxime Ethers
Kiguchi, Toshiko,Tajirii, Kazumi,Ninomiya, Ichiya,Naito, Takeaki,Hiramatsu, Hajime
, p. 253 - 256 (2007/10/02)
Tributyltin hydride-induced radical cyclization of the oxime ether 3 derived from D-glucose proceeded smoothly to give two amino alcohols 4 and 5 which were converted into two aminocyclopentitol pentaacetates 8 and 12 and 1-deoxynojirimycin known as glyco
