Synthesis of KDO Using Indium-Mediated Allylation of 2,3:4,5-Di-O-isopropylidene-D-arabinose in Aqueous Media

Gao, Jin‐Ming; Härter, Ralph; Gordon, Dana M.; Whitesides, George M.

doi:10.1021/jo00092a040

Cited by 92 publications

(35 citation statements)

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“…Other supplementary surveys regarding the effects of the single solvent or the solvent mixtures will be studied in the future. We then proceeded to screen three Brønsted acid catalysts (HCOOH, [9] AcOH, [10] and NH 4 Cl [11] ) that had previously worked well for indium-mediated reactions. HCOOH looked particularly promising on the basis of previous work by Whitesides.…”

Section: Resultsmentioning

confidence: 99%

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Three‐Component Indium‐Mediated Domino Allylation of 1H‐Indole‐3‐carbaldehyde with Electron‐Rich (Hetero)arenes: Highly Efficient Access to Variously Functionalized Indolylbutenes

Colombo¹,

Cravotto²,

Palmisano³

et al. 2008

Eur J Org Chem

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Section: Resultsmentioning

confidence: 99%

“…HCOOH looked particularly promising on the basis of previous work by Whitesides. [9] In fact, treatment of 1 with this catalyst (0.1 equiv.) at room temperature cleanly afforded 5 ( Table 1, Entry 6) in a pleasing 73 % yield; no unreacted aldehyde remained (TLC).…”

Section: Resultsmentioning

confidence: 99%

Three‐Component Indium‐Mediated Domino Allylation of 1H‐Indole‐3‐carbaldehyde with Electron‐Rich (Hetero)arenes: Highly Efficient Access to Variously Functionalized Indolylbutenes

Colombo¹,

Cravotto²,

Palmisano³

et al. 2008

Eur J Org Chem

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“…This one step transformation has conferred a change of acid labile protecting group into a base labile protecting group. Indium halides catalyzed Ferrier rearrangements of 3,4,6tri-O-alkyl-/ acyl-D-glucals and glactals (112) with number of nucleophiles provide glycosides. Indium halides catalyzed Ferrier rearrangements of 3,4,6tri-O-alkyl-/ acyl-D-glucals and glactals (112) with number of nucleophiles provide glycosides.…”

Section: Additions On Five and Six Membered Heterocyclesmentioning

confidence: 99%

“…The pyranylation has also been achieved by InCl 3 immobilized in ionic liquids [28]. InCl 3 catalysed glycosidation of per O-acetyl glycals (112)(113)(114) with alcohols in CH 3 CN under microwave irradiation provide 2,3unsaturated glycosides [29]. InCl 3 catalysed glycosidation of per O-acetyl glycals (112)(113)(114) with alcohols in CH 3 CN under microwave irradiation provide 2,3unsaturated glycosides [29].…”

Section: Additions On Five and Six Membered Heterocyclesmentioning

confidence: 99%

Indium Reagents in Heterocyclic Chemistry

Kumar

Kaur²,

Kumar

2005

COC

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Indium due to its moderate heterophilicity and recyclability plays significant role in indium catalyzed / mediated reactions of heterocycles. The co-ordination of hetero atom of the heterocycle with indium and the electronic contributions of heteroatoms in the ring provide more versatility in comparison to acyclic and carbocyclic systems. Here, the applications of indium reagents in heterocyclic chemistry have been reviewed. The review discusses the applications of indium salts -both inorganic and organometallics in the transformations of three, four, five and six membered heterocycles; synthesis of heterocycles through cycloaddition, cyclocondensation reactions, intramolecular cyclization, cascade reaction and heterocyclic modifications on the ring or on the appendage etc.

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“…13 One particularly interesting characteristic of such reactions is that they can also be carried out in air. Chan 14 and Whitesides 15 have elegantly demonstrated the potentials of such reactions with synthetic applications in carbohydrate chemistry. However, most of the successes have been limited to the use of organic halides involving an activated C-X bond (such as allyl halides).…”

Section: Introductionmentioning

confidence: 99%

Quasi-Nature Catalysis: Developing C−C Bond Formations Catalyzed by Late Transition Metals in Air and Water

2002

Acc. Chem. Res.

225

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This Account outlines the recent efforts of developing catalysis under the ambient conditions of air and water for synthetic purposes from the author's laboratory. The discussions are focused on catalytic reactions (mostly C-C bond formations) other than oxidations via late transition metals. It includes the following aspects: (1) copper-catalyzed C-C bond formations; (2) palladiumcatalyzed C-C bond formations; (3) rhodium-catalyzed C-C bond formations; (4) ruthenium-catalyzed olefin isomerizations and C-H activations. The mechanism, limitations, and synthetic applications of these reactions are also discussed.

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Synthesis of KDO Using Indium-Mediated Allylation of 2,3:4,5-Di-O-isopropylidene-D-arabinose in Aqueous Media

Cited by 92 publications

References 0 publications

Three‐Component Indium‐Mediated Domino Allylation of 1H‐Indole‐3‐carbaldehyde with Electron‐Rich (Hetero)arenes: Highly Efficient Access to Variously Functionalized Indolylbutenes

Three‐Component Indium‐Mediated Domino Allylation of 1H‐Indole‐3‐carbaldehyde with Electron‐Rich (Hetero)arenes: Highly Efficient Access to Variously Functionalized Indolylbutenes

Indium Reagents in Heterocyclic Chemistry

Quasi-Nature Catalysis: Developing C−C Bond Formations Catalyzed by Late Transition Metals in Air and Water

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