A5039101199- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Fluorine in Organic Chemistry
- Asymmetric Hydrogenation and Catalysis
- Asymmetric Synthesis and Catalysis
- Catalytic Alkyne Reactions
- Axial and Atropisomeric Chirality Synthesis
- Oxidative Organic Chemistry Reactions
- Chemical synthesis and alkaloids
- Synthesis and Catalytic Reactions
- Catalysis and Oxidation Reactions
- Synthetic Organic Chemistry Methods
- Catalytic C–H Functionalization Methods
- Vanadium and Halogenation Chemistry
- Chemical Synthesis and Analysis
- Cyclopropane Reaction Mechanisms
- Chemical Reactions and Isotopes
Institut Català d'Investigació Química
2023
Stockholm University
2020-2023
University of Sheffield
2021
3-Fluoro- and trifluoromethylthio-piperidines represent important building blocks for discovery chemistry. We report a simple efficient method to access analogs of these compounds that are armed with rich functionality allowing them be chemoselectively derivatized high diastereocontrol.
A new generation of chiral gold(I) catalysts based on variations complexes with JohnPhos-type ligands a remote C2-symmetric 2,5-diarylpyrrolidine have been synthesized different substitutions at the top and bottom aryl rings: from replacing phosphine by N-heterocyclic carbene (NHC) to increasing steric hindrance bis- or tris-biphenylphosphine scaffolds, directly attaching C2-chiral pyrrolidine in ortho-position dialkylphenyl phosphine. The tested intramolecular [4+2] cycloaddition...
A regioselective protocol for the synthesis of substituted allylic chlorides, bromides, and fluorides has been established. Remarkably, method can be applied to enantioselective challenging chiral chlorides. When halides are treated with base triazabicyclodecene as catalyst, a [1,3]-proton shift takes place, giving corresponding vinyl in excellent yields Z:E ratios. Furthermore, place an outstanding level chirality transfer from alcohols (≤98%) give trifluoromethylated
We have used experimental studies and DFT calculations to investigate the Ir
Chiral γ-branched aliphatic amines are present in a large number of pharmaceuticals and natural products. However, enantioselective methods to access these compounds scarce mainly rely on the use designed chiral transition-metal complexes. Herein, we combined an organocatalytic method for stereospecific isomerization allylic with diastereoselective reduction imine/enamine intermediates, leading γ-trifluoromethylated two noncontiguous stereogenic centers, excellent yields high diastereo-...
Enamides are versatile building blocks in organic synthesis that give access to complex nitrogen-containing compounds. However, despite the interest these compounds, synthetic strategies enamides with carbon-centered chirality atre scarce. In this work, we report an efficient method for of a new class chiral trifluoromethylated stereogenic center from easily accessible allylic amines by effective chirality-transfer process. The gives excellent yields and diastereo- enantioselectivities....
Chiral gamma-branched aliphatic amines are present in a large number of pharmaceuticals and natural products. However, enanti-oselective methods to access these compounds scarce, rely on the use designed chiral transition-metal complexes. Herein, we have combined an organocatalytic method for stereospecific isomerization allylic with dia-stereoselective reduction imine/enamine intermediates, leading gamma-trifluoromethylated two noncontiguous stereogenic centers, excellent yields high...
In this paper, we present an unprecedented and general umpolung protocol that allows the functionalization of silyl enol ethers 1,3-dicarbonyl compounds with a large range heteroatomic nucleophiles, including carboxylic acids, alcohols, primary secondary amines, azide, thiols, also anionic carbamates derived from CO2. The scope reaction extends to carbon-based nucleophiles. relies on use 1-bromo-3,3-dimethyl-1,3-dihydro-1delta3[d][1,2]iodaoxole, which provides key alpha-brominated carbonyl...
A new generation of chiral gold(I) catalysts based on variations complexes with JohnPhos-type ligands a remote C2-symmetric 2,5-diarylpyrrolidine have been synthesized different substitutions at the top and bottom aryl rings: from replacing phosphine by N-heterocyclic carbene (NHC), to increasing steric hindrance bis- or tris-biphenylphosphine scaffolds, directly attaching C2-chiral pyrrolidine in ortho-position dialkylphenyl phosphine. The cata-lysts tested intramolecular [4+2]...