- Synthetic Organic Chemistry Methods
- Catalytic Alkyne Reactions
- Asymmetric Synthesis and Catalysis
- Catalytic C–H Functionalization Methods
- Cyclopropane Reaction Mechanisms
- Oxidative Organic Chemistry Reactions
- Catalytic Cross-Coupling Reactions
- Asymmetric Hydrogenation and Catalysis
- Chemical Synthesis and Analysis
- Chemical Synthesis and Reactions
- Organometallic Complex Synthesis and Catalysis
- Microbial Natural Products and Biosynthesis
- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Synthesis of Indole Derivatives
- Fluorine in Organic Chemistry
- Chemical synthesis and alkaloids
- Coordination Chemistry and Organometallics
- Multicomponent Synthesis of Heterocycles
- Marine Sponges and Natural Products
- Vanadium and Halogenation Chemistry
- Cyclization and Aryne Chemistry
- Synthesis and Reactions of Organic Compounds
- Radical Photochemical Reactions
- Synthesis and Biological Evaluation
Universidad de Oviedo
2013-2022
Central University of the Caribbean
2022
University of South Florida
2022
ORFEO-CINQA Research Network
2020
Universidad de Burgos
2006-2015
Universidade de Vigo
2015
University of Cambridge
2000-2006
University of Bari Aldo Moro
2004
Institute for the Chemistry of OrganoMetallic Compounds
2004
Universidad de La Rioja
1999
Abstract Simple Brønsted acids such as p ‐toluenesulfonic acid monohydrate (PTS) or polymer‐bound efficiently catalyze the direct nucleophilic substitution of hydroxy group allylic and benzylic alcohols with a large variety carbon‐ heteroatom‐centered nucleophiles. Reaction conditions are mild, process is conducted under an atmosphere air without need for dried solvents, water only side product reaction.
Simple Brønsted acids such as p-toluenesulfonic acid monohydrate (PTS) efficiently catalyze a direct substitution of the hydroxyl group in propargylic alcohols with 1,3-dicarbonyl compounds. Selective propargylation or allenylation is obtained depending on nature alkynol. Reactions can be performed air undried solvents water being only side product process. By applying this reaction key step, range interesting polysubstituted furans easily synthesized one-pot procedure. [reaction: see text].
Can you dig it? An asymmetric synthesis of functionalized 1H-indenes from easily available ortho-(alkynyl)styrene derivatives under mild reaction conditions has been achieved. The reactions proceed through an unprecedented and selective 5-endo-dig gold(I)-catalyzed cycloisomerization or alkoxycyclization, if water alcohol is present (see scheme). Detailed facts importance to specialist readers are published as "Supporting Information". Such documents peer-reviewed, but not copy-edited...
The first multicomponent catalytic asymmetric synthesis of spiroacetals has been described. Hybrid molecules comprising a spiroacetal scaffold (a natural-product inspired scaffold) and an α-amino acid motif privileged fragment) are easily available through gold phosphate-catalysed one-pot three component coupling reaction alkynols, anilines glyoxylic acid.
Straightforward and efficient: Functionalized eight-membered carbocycles are easily obtained from simple allyl-substituted 5-hexyn-1-ol derivatives by a catalytic tandem sequence involving 6-exo cycloisomerization followed Prins-type cyclization (see scheme). Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2006/z503874_s.pdf or author. Please note: The publisher not responsible content functionality of any supporting supplied...
Abstract Organic acids such as PTS efficiently catalyze direct nucleophilic substitutions of the hydroxy groups propargylic alcohols with a large variety carbon‐ and heteroatom‐centered nucleophiles. Reactions can be conducted under mild conditions in air without need for dried solvents. on multigram scales are also possible. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
Take your pick! Indene-containing indole scaffolds have been catalytically prepared from C3-propargylated indoles by tandem reactions involving an initial 1,2-indole migration. This unprecedented process generates a gold carbene complex and proceeds through either formal CH insertion or Nazarov cyclization (see scheme).
The direct alkylation of 1,3-dicarbonyl compounds with benzylic alcohols is shown to be efficiently catalyzed by simple Brønsted acids such as triflic acid (TfOH) and p-toluenesulfonic (PTS) give rise monoalkylated dicarbonyl derivatives in high yields. In the absence nucleophile, substituted alkenes, generated through a formal dimerization reaction, are obtained. reactions carried out air using undried solvents, water being only side product process.
Functionalized spiroacetals have been easily prepared in a one-pot three-component coupling process that involves the reaction of pentynol derivatives, salicylaldehydes, and amines presence catalytic amounts palladium(II) complex (see scheme). Alternatively, oxygen-substituted can be obtained by using orthoesters as third component.
Abstract An efficient method for the synthesis of [3.3.1]bicyclic compounds from easily available alkynol derivatives has been developed. The reaction is based on a gold‐ or platinum‐catalyzed tandem process that involves an intramolecular hydroalkoxylation triple bond followed by Prins‐type cyclization. carried out with differently substituted and oxygen‐, nitrogen‐, carbon‐centered nucleophiles. incorporation halogen atoms as nucleophiles elimination reactions also studied....
A new and straightforward metal–organo orthogonal-relay catalytic asymmetric reaction for the enantioselective synthesis of hexahydrofuro[3,2-c]quinolines is reported. The process involves a three-component coupling between an alkynol, aldehyde arylamine catalyzed by gold complex chiral BINOL-derived phosphoric acid. Quantum chemical calculations mechanism suggest that involved acid-catalyzed Povarov better described as sequential Mannich/intramolecular Friedel–Crafts...
Abstract Simple organic acids like 2,4‐dinitrobenzenesulfonic acid (DNBSA) catalyze the Ritter reaction of secondary benzylic alcohols giving rise to corresponding N ‐benzylacetamides in usually high yields. Reactions can be conducted without exclusion oxygen and need dry solvents. With tertiary α,α‐dimethylbenzylic a different pathway involving formal dimerization takes place under acid‐catalytic conditions used. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
Three's company: Functionalized spirocyclic quinoline derivatives are easily synthesized in a one-pot three-component coupling process involving the reaction of alkynol, aldehyde, and aniline (see scheme). The is carried out presence catalytic amounts platinum(II) complex protic acid.
A novel metal-free direct arylation of unbiased arenes with diaryliodonium triflates in a process where the use solvents and additives is not required has been established.
Supply chain: the polycyclic core of (-)-berkelic acid (1) was constructed in just one step from very simple starting materials. The total synthesis 1 involves a seven-step linear sequence. Protection/deprotection steps were avoided and all but last performed on gram scale. This could solve supply problem associated with exhaustion natural source.
Abstract The dream of chemists to imitate the efficiency Nature for construction complex molecules from simple starting materials has driven development new concepts in area catalysis. In this context, “Multicomponent and Multicatalytic Reactions” have emerged as a highly valuable synthetic tool. These reactions try mimic way enzymatic machinery transforms series into intricate structures. This microreview shows some relevant multicomponent multicatalytic with intention demonstrating...
Unexpected results are obtained on treatment of alkene–zirconocene complexes with cyclic enol ethers. The ring size the ether makes reaction proceed through different mechanisms allowing Z alkenols to be prepared from furan derivatives and cyclobutanes pyran (see scheme). Supporting information for this article is available WWW under http://www.wiley-vch.de/contents/jc_2002/2004/z54151_s.pdf or author. Please note: publisher not responsible content functionality any supporting supplied by...
Abstract Direct alkylation of indoles with a wide variety tertiary propargylic alcohols under Brønsted acid catalysis conditions has been studied. A general and environmentally friendly method for the synthesis 3‐propargylated quaternary carbon atoms at their positions developed. The reactions are highly regioselective regard both to indole alkynol components. Only N ‐unsubstituted 2‐arylindoles do competitive S ′ take place afford 3‐dienyl‐ or 3‐allenylindoles, depending on moiety. were...
Progressive cycling! Highly functionalized benzofused oxabicyclo[3.3.1]nonanes are easily obtained from simple aryl-substituted alquinol derivatives by a catalytic tandem sequence involving an hydroalkoxylation reaction followed hydroarylation process, shown here.
Similar to propargylic carboxylates and sulphides, 3-propargylindoles undergo 1,2-indole migrations under cationic gold(I) catalysis. The intermediate Au-carbenoid complex may evolve through different pathways depending on the substituents at terminal positions of alkyne moiety. Thus, 3-indenylindole derivatives were easily obtained formal iso-Nazarov or Nazarov cyclizations. DFT computations support formation an alkylidenecyclopropane that undergoes gold-iso-Nazarov gold-Nazarov...
A Brønsted acid catalyzed C3-selective tert-alkylation of indoles using tertiary propargylic and benzylic alcohols has been developed. New C3-propargylated indole derivatives with a quaternary carbon at the position have efficiently synthesized. Reactions were performed in air undried solvents, water was only side product process.
The reaction of simple β-ketoesters and propargylamines under gold(III) catalysis leads to the formation elusive 2,5-dihydropyridine system. This new provides synthesis potentially bioactive compounds in moderate high yields.