A highly efficient dual catalysis approach for C-glycosylation: addition of (o-azaaryl)carboxaldehyde to glycals

Bai, Yaguang; Leng, Wei Lin; Li, Yongxin; Liu, Xuewei

doi:10.1039/c4cc06111j

Cited by 40 publications

(19 citation statements)

References 32 publications

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“…This is probably attributed to the conformationally rigid protecting group. The bicyclic torsion strain resulted in more stable compound 7 , which could be generated by proton transfer from the routinely formed Ferrier‐type glycosylated product 9f…”

Section: Resultsmentioning

confidence: 99%

Palladium‐Catalyzed Stereoselective C‐Glycosylation of Glycals with Sodium Arylsulfinates

Xiang

Jiang

et al. 2015

Eur J Org Chem

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An efficient glycosylation method to synthesize 2-deoxy-Caryl glycosides was developed. This C-glycosylation strategy is based on a palladium-catalyzed desulfitative Ferrier-type coupling reaction of glycals and sodium arylsulfinates. A [a]General Experimental Procedure: Glycal (0.15 mmol), sodium arylsulfinate (0.6 mmol), PdCl 2 (0.015 mmol), CuCl 2 (0.15 mmol), and LiCl (0.15 mmol) were added to a 25 mL Schlenk tube. MeCN (3 mL) was then added by syringe. The tube was sealed with a rubber stopper and equipped with a balloon. The mixture was heated to 75°C (external temperature) for 8-12 h. The mixture was cooled to room temperature and filtered. The filtered cake was rinsed with EtOAc. The filtrate was concentrated and purified by column chromatography on silica gel (EtOAc/hexanes) to give the desired product.

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Section: Resultsmentioning

confidence: 99%

Palladium‐Catalyzed Stereoselective C‐Glycosylation of Glycals with Sodium Arylsulfinates

Xiang

Jiang

et al. 2015

Eur J Org Chem

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“…An efficient dual-catalysis approacht oC-glycosides that involved the simultaneous activation of glycals 43 and (o-azaaryl)-carboxaldehydes 44 was described by Liu and co-workers (Scheme 12). [44] In the presence of palladium and N-heterocyclic carbene 45,t he two electrophiles, glycals 43 and (o-azaaryl)-carboxaldehydes 44,w ere activated through the formation of a p-allylÀPd complex and aB reslow intermediate, respectively.T hese two intermediates were reacted further to form the corresponding C-glycosides (46). Various carboxaldehydes and glycals with different protecting group were studied.…”

Section: C-glycosidesmentioning

confidence: 99%

“…An efficient dual‐catalysis approach to C ‐glycosides that involved the simultaneous activation of glycals 43 and ( o ‐azaaryl)‐carboxaldehydes 44 was described by Liu and co‐workers (Scheme ) . In the presence of palladium and N ‐heterocyclic carbene 45 , the two electrophiles, glycals 43 and ( o ‐azaaryl)‐carboxaldehydes 44 , were activated through the formation of a π‐allyl−Pd complex and a Breslow intermediate, respectively.…”

Section: Modification Of Sugarsmentioning

confidence: 99%

Homogeneous Catalysis: A Powerful Technology for the Modification of Important Biomolecules

Shelke

Yashmeen

Gholap

et al. 2018

Chemistry An Asian Journal

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Homogeneous catalysis plays an important and ubiquitous role in the synthesis of simple and complex molecules, including drug compounds, natural products, and agrochemicals. In recent years, the wide-reaching importance of homogeneous catalysis has made it an indispensable tool for the modification of biomolecules, such as carbohydrates (sugars), amino acids, peptides, nucleosides, nucleotides, and steroids. Such a synthetic strategy offers several advantages, which have led to the development of new molecules of biological relevance at a rapid rate relative to the number of available synthetic methods. Given the powerful nature of homogeneous catalysis in effecting these synthetic transformations, this Focus Review has been compiled to highlight these important developments.

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“…222 and 223) and was also applied to the formal synthesis of aspergillide A. In addition, Liu and co‐workers also reported the synthesis of C ‐glycosides via palladium and N ‐heterocyclic carbene‐catalyzed decarboxylative allylation through addition of ( o ‐azaaryl)carbaldehyde to glycals bearing C3‐ethylcarbonate …”

Section: Synthesis Of O‐ N‐ C‐ and S‐glycosides By Group 10 Metmentioning

confidence: 99%

Glycosylation via Transition‐Metal Catalysis: Challenges and Opportunities

Zhu

2016

Eur J Org Chem

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Development of efficient, mild, and easily operable stereoselective glycosylations is of critical importance to access sufficient amounts of pure and structurally well‐defined carbohydrates for studies of their biological functions. Such studies will facilitate our understanding of the role of complex oligosaccharides and glycoconjugates in biological processes as well as the development of carbohydrate‐based effective therapeutic agents. This review highlights recent advances in the transition metal catalyzed stereoselective glycosylations for the synthesis of a variety of structurally complex and biologically significant O‐, N‐, C‐, and S‐glycosides.

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A highly efficient dual catalysis approach for C-glycosylation: addition of (o-azaaryl)carboxaldehyde to glycals

Cited by 40 publications

References 32 publications

Palladium‐Catalyzed Stereoselective C‐Glycosylation of Glycals with Sodium Arylsulfinates

Palladium‐Catalyzed Stereoselective C‐Glycosylation of Glycals with Sodium Arylsulfinates

Homogeneous Catalysis: A Powerful Technology for the Modification of Important Biomolecules

Glycosylation via Transition‐Metal Catalysis: Challenges and Opportunities

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