Good Partnership between Sulfur and Fluorine: Sulfur-Based Fluorination and Fluoroalkylation Reagents for Organic Synthesis

Monofluorination of Organic Compounds: 10 Years of Innovation.

Through fine-tuning of reagent and base structure, sulfonyl fluorides can efficiently fluorinate diverse classes of alcohols. We show that machine learning can map the intricate reaction landscape and enable accurate prediction of high-yielding conditions for untested substrates.

Deoxyfluorination with Sulfonyl Fluorides: Navigating Reaction Space with Machine Learning.

Synthesis of Enantiopure Substituted Piperidines via an Aziridinium Ring Expansion

The 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.

https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-9-306.pdf

Stereoselectively fluorinated N-heterocycles: a brief survey.

Ring Expansion Induced by DAST: Synthesis of Substituted 3-Fluoropiperidines from Prolinols and 3-Fluoroazepanes from 2-Hydroxymethylpiperidines

Rearrangement of β-amino alcohols and application to the synthesis of biologically active compounds

Ring enlargement and ring contraction induced by DAST

The treatment of optically active prolinols with DAST produces optically active 3-fluoropiperidines via aziridinium intermediates.

Synthesis of optically active substituted 3-fluoropiperidines from prolinols by using dast

An efficient enantioselective formal synthesis of Ro 67-8867 has been achieved in 7 steps using an amino-zinc-ene-enolate cyclization and an enantioselective ring enlargement of a substituted prolinol as the key steps.

Ingrid Déchamps

Papers

Ring Expansion Induced by DAST: Synthesis of Substituted 3-Fluoropiperidines from Prolinols and 3-Fluoroazepanes from 2-Hydroxymethylpiperidines

Rearrangement of β-amino alcohols and application to the synthesis of biologically active compounds

Ring enlargement and ring contraction induced by DAST

Synthesis of optically active substituted 3-fluoropiperidines from prolinols by using dast

Efficient enantioselective formal synthesis of Ro 67-8867, a NMDA 2B receptor antagonist