Synthesis of new chiral auxiliaries derived from isosorbide

Tamion, R.; Marsais, Francis; Ribereau, P.; Quéguiner, G.; Abenhaïm, D.; Loupy, André; Munnier, L.

doi:10.1016/s0957-4166(00)80428-0

Cited by 35 publications

(14 citation statements)

References 22 publications

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“…[13] Tamion et al showed that by varying the parameters for the acetylation reaction (Ac 2 O, KOH, 120-140 8C vs. Ac 2 O, PbO, RT), both monoesters can be prepared in yields of 70 and 80 % for the exo and the endo ether, respectively. [40] By reaction of the isosorbide ditosylate with sodium ethoxide, 1,4:2,5:3,6-trianhydro-d-mannitol was obtained through Walden inversion of the exo hydroxyl group in the 2-position (Scheme 4 a). [39a, 41] Moreover, the formation of 2,5-imino-1,4:3,6-dianhydro-2,5-dideoxy-d-mannitol [42] has been ob-served, instead of that of the diamine, when the ditosylate of isoidide was reacted with methanolic ammonia to produce the diamine according to a previous method (Scheme 4 b).…”

Section: Chiral Auxiliaries and Other Chemicalsmentioning

confidence: 99%

Isosorbide as a Renewable Platform chemical for Versatile Applications—Quo Vadis?

2011

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Isosorbide is a platform chemical of considerable importance for the future replacement of fossil resource-based products. Applications as monomers and building blocks for new polymers and functional materials, new organic solvents, for medical and pharmaceutical applications, and even as fuels or fuel additives are conceivable. The conversion of isosorbide to valuable derivatives by functionalization or substitution of the hydroxyl groups is difficult because of the different configurations of the 2- and 5-positions and the resulting different reactivity and steric hindrance of the two hydroxyl groups. Although a substantial amount of work has been published using exclusively the endo or exo derivatives isomannide and isoidide, respectively, as starting material, a considerable effort is still necessary to transfer and adapt these methods for the efficient conversion of isosorbide. This Minireview deals with all aspects of isosorbide chemistry, which includes its production by catalytic processes, special properties, and chemical transformations for its utilization in biogenic polymers and other applications of interest.

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Section: Chiral Auxiliaries and Other Chemicalsmentioning

confidence: 99%

Isosorbide as a Renewable Platform chemical for Versatile Applications—Quo Vadis?

2011

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“…[15] Subsequently, tosylate 4 was converted into thiazolium 5 by heating with a large excess of thiazole at 80°C. [16] However, no product was detected even after 2 d.…”

Section: Synthesis Of Chiral Azolium Salt Precursors To Nhc Ligands Dmentioning

confidence: 97%

Asymmetric Transfer Hydrogenation of Aromatic Ketones Using Rhodium Complexes of Chiral N‐Heterocyclic Carbenes Derived from (S)‐Pyroglutamic Acid

2011

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“…[46] To our knowledge, there is only one example using nitrogen-containing isohexide as a chiral auxiliary. In 1993, Quéguiner reported for the first time the synthesis of chiral aminoethers 27 [41] and their use in the asymmetric alkylation of phenylacet amides 28 (Scheme 5). The best diastereomeric ratio was evaluated at 83% when running the reaction at -100°C with R 1 = cyclohexyl.…”

Section: Application To Asymmetric Inductionmentioning

confidence: 99%

“…Lower yields (45 and 31%) and epimerization were observed with aniline and N-ethylaniline. [41] N-Methylimidazole reacted with phenylsulfonate 20a in 50% yield after 4 h…”

Section: Nucleophilic Substitution Of Activated Isohexidesmentioning

confidence: 99%