A rapid stereoselective C-glycosidation of indoles and pyrrole via indium trichloride promoted reactions of glycosyl halides

Mukherjee, Debaraj; Sarkar, Sujit; Chowdhury, Uday Shankar; Taneja, Subash C.

doi:10.1016/j.tetlet.2006.11.107

Cited by 41 publications

(25 citation statements)

References 41 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Interestingly, uncatalyzed electrophilic allylation and benzylation of indoles with the corresponding organo halides was recently reported by Westermaier and Mayr through the assistance of neutral aqueous or alcoholic solutions 117d. Moreover, the stereoselective C‐glycosidation of substituted indoles with glycosyl bromides was reported to be efficiently catalyzed by InCl 3 (10 mol %) 117e…”

Section: Reaction With C(sp3)‐based Alkylating Agentsmentioning

confidence: 97%

Catalytic Functionalization of Indoles in a New Dimension

2009

View full text Add to dashboard Cite

140 years ago Adolf von Baeyer proposed the structure of a heteroaromatic compound which revolutionized organic and medical chemistry: indole. After more than a century, indole itself and the complexity of naturally occurring indole derivatives continue to inspire and influence developments in synthetic chemistry. In particular, the ubiquitous presence of indole rings in pharmaceuticals, agrochemicals, and functional materials are testament to the ever increasing interest in the design of mild and efficient synthetic routes to functionalized indole derivatives. This Review emphasizes the achievements in the selective catalytic functionalization of indoles (C-C bond-forming processes) over the last four years.

show abstract

Section: Reaction With C(sp3)‐based Alkylating Agentsmentioning

confidence: 97%

Catalytic Functionalization of Indoles in a New Dimension

2009

View full text Add to dashboard Cite

show abstract

“…Thus, C-glycosyl indoles and pyrroles were prepared within a few minutes through the coupling of acetylated glycosyl bromides with indoles and pyrroles in the presence of indium(III) chloride (10 mol%). 254 Similarly, O-glycosylation was performed through the coupling of acetylated glycosyl bromides with alcohols in the presence of indium(III) chloride (40 mol%), thereby providing the corresponding O-glycosides with pronounced b-selectivity owing to the presence of a participating group at the C2 position. 255 With thiols instead of alcohols, peracetylated sugars were reactive enough to afford the corresponding b-thioglycosides, but the presence of titanium(IV) chloride (20 mol%) along with indium(III) chloride (20 mol%) was required.…”

Section: Ferrier Rearrangement and Glycosylationmentioning

confidence: 99%

Recent Advances in Indium-Promoted Organic Reactions

Augé¹,

Lubin‐Germain²,

Uziel³

2007

Synthesis

162

View full text Add to dashboard Cite

I n d i u m -P r o m o t e d O r g a n i c R e a c t i o n sAbstract: This review deals with organic reactions which are promoted by indium metal or indium salts, with a focus on recent advances in stoichiometric and catalytic pathways. Applications to transmetalations, cross-coupling reactions and carboindation, in which an organoindium species may be postulated, are highlighted, as well as the reactions in which a radical is the key intermediate. Special attention is placed on the role of indium metal as a reducer, and on the Lewis acidity of indium salts in catalytic processes.

show abstract

“…_ 8 ) T D $ F I G ] aromatic moieties. The introduction of indole species has been described with excellent a-selectivities using indium (III) chloride as an activator (Scheme 15) [114].…”

Section: [ ( S C H E M E _ 1 4 ) T D $ F I G ]mentioning

confidence: 99%