Epoxides samarium iodide

Carree, F. Gil, R. Collin, J. (2004) Samarium iodides catalyzed meso-epoxides ring opening by aromatic amines.. Tetrahedron Lett., 45 7749-7751. [Pg.340]

Both samarium iodide and ytterbium triisopropoxide catalyse the ring opening45 of epoxides by TMS-azide in the latter case, due to an acidic work-up, the products are isolated as vicinal azido alcohols. [Pg.1672]

Samarium iodide has also been used for reducing epoxides to alkenes. Compared with other low-valent metal systems this reagent requires prolonged reaction time at room temperature, but the stereoselectivity, with c -epoxides giving m-alkenes, is high. " ... [Pg.889]

Sml2X that is produced as a result of this process then serves to open the epoxide, generating the iodohy-drin. Although this appears to be a likely scenario, a more direct route involving a Finkelstein reaction between the brsamarium iodide salts - cannot be ruled out (Scheme 2). [Pg.261]

Other a-alkoxylithium carbanions have been generated by tin-lithium exchange at low temperature, by metallation of (alkoxymethyl)trimethylsilane, or by using samarium iodide. These reagents do not directly form epoxides due to the poor nucleofiigicity of alkoxide anion. However, the resultant protected diols can be considered as particularly robust precursors to epoxides when deprotected and manipulated in any number of standard ways. A notable example of this strategy is shown in Scheme 13. ... [Pg.829]

Vinyl epoxides (267) undergo rapid rearrangement when treated with samarium iodide at -90°C, using ethanol as the proton source,... [Pg.139]

The Ishii group <00TL3389> reported an interesting samarium iodide promoted reaction of epoxides e.g., 105) with imincs (e.g., 106) to form oxazolidines (e.g., 107). The mechanism proceeds through a radical pathway. The radical chemistry of epoxides has been the subject of a recent review <01T1>. [Pg.64]

A related reaction transforms non-racemic a-hydroxy epoxides (43) into 2-quartemary-1,3-diol monoesters (44) under the influence of samarium iodide and an aldehyde. Though 43 was used as a mixture of diastereomers, only one product diastereomer was observed. [Pg.328]

EPOXIDES Diphosphorus tetraiodide. Lithium. 3-Methyl-2-selenoxo-l,3-benzothiazole. Phosphorus triiodide. Lithium. Potassium iodide-Zinc-Phos-phorus(V) oxide. Samarium(II) iodide. Sodium O.O-diethyl phosphorotelluro-ate. Triphenylphosphine hydroiodide-Triplienylphosphine diiodide. [Pg.467]

Arene(tricarbonyl)chromium complexes, 19 Nickel boride, 197 to trans-alkenes Chromium(II) sulfate, 84 of anhydrides to lactones Tetrachlorotris[bis(l,4-diphenyl-phosphine)butane]diruthenium, 288 of aromatic rings Palladium catalysts, 230 Raney nickel, 265 Sodium borohydride-1,3-Dicyano-benzene, 279 of aryl halides to arenes Palladium on carbon, 230 of benzyl ethers to alcohols Palladium catalysts, 230 of carboxylic acids to aldehydes Vilsmeier reagent, 341 of epoxides to alcohols Samarium(II) iodide, 270 Sodium hydride-Sodium /-amyloxide-Nickel(II) chloride, 281 Sodium hydride-Sodium /-amyloxide-Zinc chloride, 281 of esters to alcohols Sodium borohydride, 278 of imines and related compounds Arene(tricarbonyl)chromium complexes, 19... [Pg.372]

From epoxides by reduction Samarium(II) iodide, 270 Sodium hydride-Sodium /-amyloxide-Nickel(II) chloride, 281 Sodium hydride-Sodium /-amyloxide-Zinc chloride, 281... [Pg.377]

Salicylate annelation, 279-280 Salutaridines, 593 Samarium(ll) iodide, 464-465 Sarkomycin, 457, 458 Schweizer s reagent, 597 Selenium, 465-466 Selenones, 123 Selenuranes, 223 Shapiro reaction, 563-565 Sharpless epoxidation, 263, 600 Shikimic acid, 3, 4, 548 Sibirinone, 596 Sila-Pummerer reaction, 576 Silica, 466... [Pg.338]

Molander, G.A., and del Pozo Losada, C., Sequenced reactions with samarium(II) iodide. Domino epoxide ring-openingZketyl olefin coupling reactions, 7. Org. Chem., 62, 2935, 1997. [Pg.323]

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