Ring enlargement and ring contraction induced by DAST

Ferret, Haidy; Déchamps, Ingrid; Pardo, Domingo Gomez; Hijfte, Luc Van; Cossy, A.

doi:10.3998/ark.5550190.0011.812

Cited by 24 publications

(24 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A unique complication sometimes arises when deoxyfluorination is attempted in N -heterocyclic systems: side reactions can occur, bought about by neighbouring group participation (Scheme 4) [58]. Such processes can lead to rearrangement, and this outcome has been rationally exploited to synthesise fluorinated five- [59], six- [60] and seven-membered [61] N -heterocycles that may have been otherwise difficult to access (e.g.…”

Section: Reviewmentioning

confidence: 99%

Stereoselectively fluorinated N-heterocycles: a brief survey

Hu¹,

Hunter²

2013

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

SummaryThe stereoselective incorporation of fluorine atoms into N-heterocycles can lead to dramatic changes in the molecules’ physical and chemical properties. These changes can be rationally exploited for the benefit of diverse fields such as medicinal chemistry and organocatalysis. This brief review will examine some of the effects that fluorine substitution can have in N-heterocycles, including changes to the molecules’ stability, their conformational behaviour, their hydrogen bonding ability, and their basicity. Finally, some methods for the synthesis of stereoselectively fluorinated N-heterocycles will also be reviewed.

show abstract

Section: Reviewmentioning

confidence: 99%

Stereoselectively fluorinated N-heterocycles: a brief survey

Hu¹,

Hunter²

2013

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…A Staudinger reduction of the azide groups followed by hydrogenolysis of the benzyl ethers gave 29. The treatment of 26 with Tf2O in pyridine/CH2Cl2 followed by SN2 displacement with acetate and Zemplén deacetylation afforded a 4'-epi derivative (30). Compound 30 was treated with Tf2O and TBAF to give a 4'-deoxy-4'-fluorinated derivative (28).…”

Section: Pagementioning

confidence: 99%

“…The principal obstacle to fluorination of aminoglycosides is obtaining an appropriately protected molecule in which only the target group is free to transform; this process may require several well-planned protection-deprotection sequences. 29 Sometimes, the outcome of deoxyfluorination is difficult to predict a priori, 30 and several steps are required to achieve the desired substitution pattern, obtaining a single fluorinated AG derivative can be considered a scientific feat in and of itself.…”

Section: Introductionmentioning

confidence: 99%

Fluorinated aminoglycosides

Saavedra¹,

Vilchis‐Reyes²

2019

Arkivoc

View full text Add to dashboard Cite

Aminoglycosides (AGs) are natural or semisynthetic antibiotics that are inherently toxic, and their use is limited by the widespread presence of AG-resistant bacteria. However, AGs are still valued members of the antibiotic arsenal, particularly against Gram-negative bacteria. The efficiency and clinical value of this class of antibiotics have motivated the exploration of strategies to overcome or evade both the antimicrobial resistance and toxicity. The incorporation of a fluorine atom into AGs has attracted attention as a potential strategy to solve these problematics. This review provides an overview of the research on fluorinates aminoglycosides, their synthesis and, when available, their antimicrobial activity, relative toxicity toward mice or human cells and physicochemical properties.

show abstract

“…Diethylaminosulfur trifluoride (DAST) has been widely used for directly replacing a hydroxyl group by fluorine under very mild conditions. 2,3 Nevertheless, the corrosive properties of DAST make it unsuitable for high-scale usage. In this context, commercially available aminodifluorosulfinium salts, 4 such as XtalFluor-E (1) or XtalFluor-M (2), are efficient alternatives.…”

Section: Introductionmentioning

confidence: 99%