Hf(OTf)4-Catalyzed Three-Component Synthesis of N-Carbamate-Protected β-Amino Ketones

Chen, Zhenzhen; Yang, Dong-Zhao; Dong, Yingying; Chi, Mei; Pu, Shouzhi; Sun, Qi

doi:10.3390/molecules27031122

Cited by 2 publications

(2 citation statements)

References 46 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…But the same reactions proceed smoothly even at room temperature in the presence of catalytic amounts of iodine [73] or hafnium (IV) triflate. [74] For example, benzyl carbamate is added to various chalcones under mild conditions to give aza-Michael adducts in high yields. In the first case, acetonitrile is found to be the best choice as a solvent.…”

Section: Amides Carbamates Hydrazides and Uracilesmentioning

confidence: 99%

Weak Nucleophiles in the Aza‐Michael Reaction

Rulev

2023

Adv Synth Catal

View full text Add to dashboard Cite

The 1,4‐conjugated addition of nitrogen centered nucleophiles to electron‐deficient alkenes is one of the most significant and widely used reactions in modern synthetic organic chemistry. To date, various protocols for the aza‐Michael reaction have been developed. However, these reports mainly focus on the use of strong Michael donors. In recent years, the conjugate addition of weak nitrogen nucleophiles to various Michael acceptors gained increasing popularity. Impressive progress in this area has been achieved by the use of more efficient catalyst systems. This review aims to provide a critical analysis of the results obtained in reactions of weak nucleophiles (azoles, pyrroles, indoles, carbamates, purines, amides, hydrazides, uraciles etc) with electron‐deficient alkenes which were reported over the past twelve years.

show abstract

Section: Amides Carbamates Hydrazides and Uracilesmentioning

confidence: 99%

Weak Nucleophiles in the Aza‐Michael Reaction

Rulev

2023

Adv Synth Catal

View full text Add to dashboard Cite

show abstract

“…To address this issue, strong Lewis acids or Bronsted acids are required for glycosylation, and elevating temperature and microwave are other improvement strategies used to convert oxazoline derivatives to the corresponding glycosides. Of note, among common rare earth metal triflates, hafnium (IV) tetratriflate was found to be a good promoter, which was widely applicable to a variety of reactions, such as glycosylation reactions ( Manabe and Ito, 2013 ; Chen and Zhang, 2017 ; Wang et al, 2018 ) and β -carbamate ketones ( Chen et al, 2022 ).…”

Section: Introductionmentioning

confidence: 99%

Selective synthesis of α- and β-glycosides of N-acetyl galactosamine using rare earth metal triflates

Wang

Zhang²,

Cao³

et al. 2022

Front. Chem.

View full text Add to dashboard Cite

Structures containing galactose and GalNAc residues are specifically recognized by asialoglycoprotein receptors, allowing them to selectively internalize by hepatocytes for drug-targeting delivery. However, methods for direct synthesis of GalNAc glycosides are still challenging due to the poor participating group of 2-acetamido. Here, we develop a facile strategy to synthesize various GalNAc glycosides by employing a series of rare earth metal triflates, and the results demonstrate that both α-glycosides and β-glycosides of GalNAc can be obtained by conducting with Hf(OTf)4 and Sc(OTf)3, respectively. These applicable results indicate that any interested GalNAc-containing substrates could be prepared by this simple strategy.

show abstract

Hf(OTf)4-Catalyzed Three-Component Synthesis of N-Carbamate-Protected β-Amino Ketones

Cited by 2 publications

References 46 publications

Weak Nucleophiles in the Aza‐Michael Reaction

Weak Nucleophiles in the Aza‐Michael Reaction

Selective synthesis of α- and β-glycosides of N-acetyl galactosamine using rare earth metal triflates

Contact Info

Product

Resources

About