2015
DOI: 10.3762/bjoc.11.150
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Cross-metathesis reaction of α- and β-vinyl C-glycosides with alkenes

Abstract: SummaryCross-metathesis of α- and β-vinyl C-deoxyribosides and α-vinyl C-galactoside with various terminal alkenes under different conditions was studied. The cross-metathesis of the former proceeded with good yields of the corresponding products in ClCH2CH2Cl the latter required the presence of CuI in CH2Cl2 to achieve good yields of the products. A simple method for the preparation of α- and β-vinyl C-deoxyribosides was also developed. In addition, feasibility of deprotection and further transformations were… Show more

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Cited by 5 publications
(5 citation statements)
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“…Although lots of transitional metal‐catalyzed cross coupling including Heck, Suzuki, Stille and Negishi‐type reactions have been developed for the synthesis of C‐glycosides using glycals, the functional regioselectivity and α / β stereoselectivity at the anomeric carbon constitute are still one of the most challenging issues in carbohydrate chemistry . For example, Ernest's group utilized Pd 0 ‐mediated cyclo‐etherification of 1‐acetoxy‐2,3‐dideoxy‐oct‐2‐enitols to produce C‐vinyl α ‐ and β ‐glycopyranosides with high stereoselectivity using ( S , S ) or ( R , R )‐DACH ligands in 2014 (Scheme ), and then Martin's group produced epimeric mixture of C‐vinyl deoxyriboside by the Lindlar hydrogenation of the epimeric mixture of C‐ethynyl deoxyriboside . Liu's group reported a palladium‐catalyzed one‐pot Tsuji‐Trost type decarboxylative allylation/Wittig reaction to synthesize β ,( E )‐selective C‐vinyl glycosides with pyridyl group containing aldehydes and β ,( Z )‐selective C‐vinyl glycosides with nonpyridyl aldehydes in 2017, which had potential to be applied in synthesizing C‐vinyl glycosides in high efficiency with controlled diastereoselectivity …”
Section: Figurementioning
confidence: 99%
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“…Although lots of transitional metal‐catalyzed cross coupling including Heck, Suzuki, Stille and Negishi‐type reactions have been developed for the synthesis of C‐glycosides using glycals, the functional regioselectivity and α / β stereoselectivity at the anomeric carbon constitute are still one of the most challenging issues in carbohydrate chemistry . For example, Ernest's group utilized Pd 0 ‐mediated cyclo‐etherification of 1‐acetoxy‐2,3‐dideoxy‐oct‐2‐enitols to produce C‐vinyl α ‐ and β ‐glycopyranosides with high stereoselectivity using ( S , S ) or ( R , R )‐DACH ligands in 2014 (Scheme ), and then Martin's group produced epimeric mixture of C‐vinyl deoxyriboside by the Lindlar hydrogenation of the epimeric mixture of C‐ethynyl deoxyriboside . Liu's group reported a palladium‐catalyzed one‐pot Tsuji‐Trost type decarboxylative allylation/Wittig reaction to synthesize β ,( E )‐selective C‐vinyl glycosides with pyridyl group containing aldehydes and β ,( Z )‐selective C‐vinyl glycosides with nonpyridyl aldehydes in 2017, which had potential to be applied in synthesizing C‐vinyl glycosides in high efficiency with controlled diastereoselectivity …”
Section: Figurementioning
confidence: 99%
“…[8] Generally, C-glycosylation reactions can involve glycosyl electrophilic/cationic species, anionic species, radical species, or transition-metal complexes. [12] Liu's group reported a palladium-catalyzed one-pot Tsuji-Trost type decarboxylative allylation/Wittig reaction to synthesize b,(E)-selective C-vinyl glycosides with pyridyl group containing aldehydes and b,(Z)selective C-vinyl glycosides with nonpyridyl aldehydes in 2017, which had potential to be applied in synthesizing C-vinyl glycosides in high efficiency with controlled diastereoselectivity. [9] Although lots of transitional metal-catalyzed cross coupling including Heck, Suzuki, Stille and Negishi-type reactions have been developed for the synthesis of C-glycosides using glycals, the functional regioselectivity and a/b stereoselectivity at the anomeric carbon constitute are still one of the most challenging issues in carbohydrate chemistry.…”
mentioning
confidence: 99%
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“…In other syntheses the construction of the C=C bond in styrenes F are realized in one step: dehydration reaction of O ‐perbenzylated or O ‐peracetylated 1‐phenyl‐2‐(β‐ d ‐glucopyranosyl)ethanol H , prepared from free aldoses in three‐step reactions or the Julia olefination of the O ‐perbenzylated β‐ C ‐glucopyranosyl aldehyde I resulted in C ‐glycopyranosyl styrenes F . Another possibility is the formation of the C=C bond in a cross‐metathesis reaction between a vinyl α‐ C ‐ d ‐galactopyranoside J with alkenes in the presence of Hoveyda‐Grubbs II catalyst and CuI …”
Section: Introductionmentioning
confidence: 99%