A5058475033- Asymmetric Synthesis and Catalysis
- Asymmetric Hydrogenation and Catalysis
- Synthetic Organic Chemistry Methods
- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Innovative Microfluidic and Catalytic Techniques Innovation
- Chemical Synthesis and Analysis
- Synthesis and Catalytic Reactions
- Chemical Synthesis and Reactions
- Oxidative Organic Chemistry Reactions
- Cyclopropane Reaction Mechanisms
- Synthesis of Indole Derivatives
- Organic Chemistry Cycloaddition Reactions
- Catalytic C–H Functionalization Methods
- Crystallography and molecular interactions
- Click Chemistry and Applications
- Axial and Atropisomeric Chirality Synthesis
- Chemical synthesis and alkaloids
- Nanomaterials for catalytic reactions
- Analytical Chemistry and Chromatography
- Photochromic and Fluorescence Chemistry
- Marine Toxins and Detection Methods
- Model-Driven Software Engineering Techniques
- Catalytic Alkyne Reactions
- Sulfur-Based Synthesis Techniques
Institut Català d'Investigació Química
2012-2022
Cornell University
2019
Catalonian Research and Innovation Centre
2019
Barcelona Institute for Science and Technology
2016-2018
Shanghai Institute for Science of Science
2016-2018
Institute of Science and Technology
2016-2018
University of St Andrews
2017
Philadelphia University
2015
Universitat de Barcelona
2007-2014
Aarhus University
2011-2013
A new concept in organocatalysis allowing for the construction of cyclobutanes with four contiguous stereocenters complete diastereo- and enantiomeric control by a formal [2 + 2]-cycloaddition is presented. The based on simultaneous dual activation α,β-unsaturated aldehydes nitroolefins amino- hydrogen-bonding catalysis, respectively. bifunctional squaramide-based aminocatalyst has been designed synthesized order to enable such an strategy. potential scope reaction are demonstrated,...
The fast and highly stereoselective Mannich reaction of aldehydes ketones with the N-(p-methoxyphenyl) ethyl glyoxylate imine catalyzed by polystyrene resins functionalized (2S,4R)-hydroxyproline is reported. effect nature linker connecting proline polymeric backbone has been studied, a 1,2,3-triazole constructed from azidomethyl O-propargyl hydroxyproline turns out to be optimal for catalytic activity enantioselectivity. With aldehyde donors, reactions leading complete conversion in 1-3 h...
Giving directions: Optically active dihydropyrans bearing three contiguous stereogenic centers can be efficiently prepared by the title reaction. High stereo- and regiocontrol achieved employing a bifunctional H-bond-directing aminocatalyst. Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents peer-reviewed, but not copy-edited or typeset. They made available submitted authors. Please note: The publisher is responsible for content...
Abstract Sustainability concerns are reshaping the way chemists work, not only at stage of process design, but also when actually performing reactions. This change in outlook is exemplified by deployment continuous flow techniques, which slowly becoming mainstream practice. Indeed, possibility catalytic processes (the flagship sustainable chemistry) presents distinctive advantages. Thus, several authors focusing their efforts on trying to get best these two worlds, with consequent challenge...
Abstract A polystyrene‐supported 1,1’‐bi‐2‐naphthol derived phosphoric acid has been synthesized and applied in the enantioselective Friedel–Crafts reaction of indoles sulfonylimines. The immobilized catalyst was highly active selective, gave rise to a broad range 3‐indolylmethanamines (19 examples) high yields excellent enantioselectivities (up 98 % enantiomeric excess) after short times under very convenient conditions (RT dichloromethane). Moreover, repeated recycling (14 cycles) possible...
The widely applicable TRIP phosphoric acid catalyst has been immobilized on polystyrene using a copolymerization-based strategy. resin (PS-TRIP) proven to be highly active and enantioselective in the asymmetric allylboration of aldehydes. Moreover, it shown extremely robust, as can reused for 18 times, after which still retained its activity. Lastly, further prove benefits immobilization, continuous flow experiment spanning 28 h carried out with very high yields ee's.
A polystyrene-supported isothiourea (1a) behaves as a highly efficient organocatalyst in variety of formal [4 + 2] cycloaddition reactions. The catalytic system has proven to be versatile, leading six-membered heterocycles and spiro-heterocycles bearing an oxindole moiety high yields very enantioselectivities (32 examples, including the previously unreported spiropyranopyrazolones 8; 97% mean ee). notable chemical stability 1a under operation conditions results recyclability (11 cycles,...
A polystyrene (PS) supported bifunctional squaramide organocatalyst promotes fast Michael addition of 2-hydroxy-1,4-naphthoquinone to nitroalkenes with very high enantioselectivities at low catalyst loadings. The can be recycled up 10 times without any decrease in enantioselectivity (average 96% ee) and adapted continuous flow operation (24 h). single experiment involving six different a sequential manner highlights the applicability this methodology for rapid access chemical diversity.
A series of azobenzene-based thiourea catalysts have been developed with the aim achieving control over catalytic activity by use light. The conceptual design these systems relies on inactivation means intramolecular hydrogen bonding, only likely to take place in one their isomeric forms. After fine structure modulation catalyst a substantial difference has observed between irradiated and nonirradiated reaction. Furthermore, system allowed situ manipulation during course given experiment.
Higher-order cycloaddition reactions constitute an efficient approach towards the construction of medium to large ring systems. However, enantioselective versions these transformations remain scarce, which hampers their deployment in medicinal chemistry, or any other discipline homochirality is deemed crucial. Herein, we report a novel method for production enantiomerically enriched cycloheptatrienes fused pyrrolidone on basis isothiourea-catalyzed periselective [8+2] reaction between chiral...
An efficient, highly regio- and stereoselective [4 + 2] cycloaddition reaction to generate tetrahydropyranopyrazole frameworks has been developed. To this end, a dienamine-based catalytic strategy that relies on the H-bond-directing effect of hydroxy group dinaphthylprolinol-type aminocatalyst used. This enables synthesis multifunctionalized heterocyclic derivatives with three contiguous stereocenters in good yields excellent enantioselectivities.
Abstract Light-regulated drugs allow remotely photoswitching biological activity and enable plausible therapies based on small molecules. However, only freely diffusible photochromic ligands have been shown to work directly in endogenous receptors methods for covalent attachment depend genetic manipulation. Here we introduce a chemical strategy covalently conjugate photoswitch the of proteins demonstrate its application kainate receptor channel GluK1. The approach is photoswitchable...
Der Anglerfisch-Katalysator: Die Aktivierung von Anthracenen durch Aminokatalyse (siehe Schema) ermöglicht [4+2]-Cycloadditionen mit gleichzeitigem Aromatizitätsverlust bei Raumtemperatur und niedriger Katalysatorkonzentration. Eine hoch enantioselektive Diels-Alder-Reaktion Nitroalkenen als Dienophilen wurde ebenfalls entwickelt. Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents peer-reviewed, but not copy-edited or typeset. They...
A novel polymer-supported fluorinated organocatalyst has been prepared and benchmarked in the enantioselective Michael addition of aldehydes to nitroalkenes. The system proven be highly efficient displays excellent selectivities (er dr) with a wide variety substrates. Detailed deactivation studies have given valuable insights, thus allowing lifespan this immobilized aminocatalyst significantly extended. These data facilitated implementation enantioselective, continuous flow processes either...
A set of six solid-supported diarylprolinol catalysts (varying on the anchoring strategy and type polymeric support) has been prepared applied to enantioselective cyclopropanation reaction. The selected candidate allows implementation a long flow experiment (48 h) generates library 12 cyclopropanes by sequential experiments. mildness utility method have enabled telescoped process in which outstream is directly used Wittig
A new, cost-effective polystyrene-supported squaramide organocatalyst has been shown to mediate the highly enantioselective formation of pyranonaphthoquinones in flow through a sequential two-step process.
N-Heterocyclic carbene catalysts are used for the first time to mediate asymmetric [8 + 2] cycloadditions of enals with tropones. The kinetic cis-cycloadducts can be epimerized their trans analogues by simply using increased amounts base and longer reaction times. Substituted tropones also tolerated, cycloaddition products derivatized hydrogenation or methanolysis. main stereochemical features process have been rationalized microkinetic modeling based on results DFT calculations.
Enantiomerically pure aryl and benzyl glycidyl ethers undergo stereospecific cyclizations leading to 3-chromanols or tetrahydrobenzo[c]oxepin-4-ols under mild conditions in the presence of a catalytic amount FeBr3/3AgOTf. The same processes are also mediated, albeit much less efficient manner, by AuCl3/3AgOTf. set active mediators this group (BF3 x Et2O, FeBr3, FeBr3/3AgOTf, AuCl3/3AgOTf) shows its nature as Friedel-Crafts reactions disfavors intermediacy arylgold species.
[Au(tmbn)2](SbF6) is the first gold(I) complex supported by two nitrile ligands that indefinitely stable at room temperature. This a highly versatile precatalyst can be used for preparation of active and robust solid-supported catalysts.
A polystyrene-supported analog (PS-PIB) of 3-exo-morpholinoisoborneol (MIB), designed for increased chemical stability, has been synthesized and used as a ligand in the asymmetric alkylation aldehydes with Et2Zn. The supported turned out to be highly active enantioselective broad scope substrates (92–99% ee), allowing repeated recycling. single-pass, continuous flow process implemented PS-PIB shows only marginal decrease conversion after 30 h operation.
A PS-immobilized thiourea catalyses the enantioselective α-amination of dicarbonyl compounds at room temperature. It is not deactivated by azodicarboxylate reagents, allowing multiple recycling in batch as well use flow (21 min residence time).
A song of ice and fire! The usually innocent paraldehyde can be used as an acetaldehyde precursor in organocatalytic asymmetric Michael addition (see scheme) thanks to the proper combination two immobilized catalysts. site isolation induced by polymeric supports has proven crucial preclude deactivation otherwise incompatible
Heterogenized versions of the second-generation MacMillan imidazolidin-4-one are described for first time. This versatile organocatalyst has been supported on 1% DVB Merrifield resin and Fe3O4 magnetic nanoparticles through a copper-catalyzed alkyne–azide cycloaddition (CuAAC) reaction. The resulting catalytic materials have successfully applied to asymmetric Friedel–Crafts alkylation indoles with α,β-unsaturated aldehydes. While both systems can be easily recovered admit repeated recycling,...
A polystyrene-supported isothiourea catalyst, based on the homogeneous catalyst HyperBTM, has been prepared and used for acylative kinetic resolution of secondary alcohols. wide range alcohols, including benzylic, allylic, propargylic cycloalkanol derivatives, a 1,2-diol, resolved using either propionic or isobutyric anhydride with good to excellent selectivity factors obtained (28 examples, s values up 600). The can be recovered reused by simple filtration washing sequence, no special...