A5024183244- Chemical Synthesis and Reactions
- Asymmetric Synthesis and Catalysis
- Organic Chemistry Cycloaddition Reactions
- Chemical Synthesis and Analysis
- X-ray Diffraction in Crystallography
- Synthetic Organic Chemistry Methods
- Synthesis and Catalytic Reactions
- Crystallization and Solubility Studies
- Ferrocene Chemistry and Applications
- Peroxisome Proliferator-Activated Receptors
- Catalytic Cross-Coupling Reactions
- Oxidative Organic Chemistry Reactions
- Cyclopropane Reaction Mechanisms
- Synthesis and Biological Evaluation
- Sulfur-Based Synthesis Techniques
- Chemical synthesis and pharmacological studies
- Crystallography and molecular interactions
- Catalytic C–H Functionalization Methods
- Inflammatory mediators and NSAID effects
- Neurological Disorders and Treatments
- Polyoxometalates: Synthesis and Applications
- Antiplatelet Therapy and Cardiovascular Diseases
- Monoclonal and Polyclonal Antibodies Research
- Asymmetric Hydrogenation and Catalysis
- Click Chemistry and Applications
Eli Lilly (Spain)
2008-2024
Instituto de Química Orgánica General
1996-2006
Consejo Superior de Investigaciones Científicas
1996-2006
IIT@MIT
2004
Instituto de Química Física Blas Cabrera
1998-2003
Universidad Autónoma de Madrid
1999-2003
Universidad San Pablo CEU
2003
Massachusetts Institute of Technology
2003
University of Castilla-La Mancha
2002
Universidad de Alcalá
1994-1997
Lipoprotein(a) (Lp(a)), an independent, causal cardiovascular risk factor, is a lipoprotein particle that formed by the interaction of low-density (LDL) and apolipoprotein(a) (apo(a))
The first detailed study of the palladium-catalyzed amination aryl nonaflates is reported. Use ligands 2-4 and 6 allows for catalytic electron-rich -neutral with both primary secondary amines. With use Xantphos 5, a variety functionalized resulted in excellent yields anilines; even 2-carboxymethyl nonaflate effectively coupled alkylamine. Moderate were obtained when coupling halo-aryl amines, where most cases reacted preference to halide. Overall, are an effective alternative triflates C-N...
The synthesis of a wide structural variety enantiopure 1-phosphino-2-sulfenylferrocene ligands 1 possessing exclusively planar chirality is described. In the case readily available tert-butylsulfenyl derivatives very high enantioselectivities were obtained in palladium-catalyzed allylic substitution 1,3-diphenyl-2-propenyl acetate with dimethyl malonate (ee's up to 97%) and nitrogen nucleophiles 99.5%). Palladium complexes these ferrocenes characterized by NMR X-ray diffraction, revealing...
DNA-encoded library technology (ELT) has emerged in the pharmaceutical industry as a powerful tool for hit and lead generation. Over last 10 years, number of DNA-compatible chemical reactions have been published used to synthesize libraries. Among most commonly medicinal chemistry is C–N bond formation, its application affords an alternative approach identify high-affinity binders biologically relevant protein targets. Herein we report newly developed Pd-promoted cross coupling reaction...
A simple and modulable access to a structural variety of enantiopure amino-substituted ferrocenyl sulfoxides their use as chiral catalysts in the asymmetric addition diethylzinc aromatic aldehydes is described. Moderate high enantioselectivities (up 96% ee) were obtained case arylsulfonamide ligands (R(Fc), R(S))-4h R(S))-4i. It has been demonstrated that planar chirality ferrocene unit decisive element involved reaction.
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXT4-Alkyl-1,4-dihydropyridine derivatives as specific PAF-acether antagonistsCarlos E. Sunkel, Miguel Fau de Casa-Juana, Luis Santos, M. Mar Gomez, Mercedes Villarroya, Antonia Gonzalez-Morales, Jaime G. Priego, and Pilar OrtegaCite this: J. Med. Chem. 1990, 33, 12, 3205–3210Publication Date (Print):December 1, 1990Publication History Published online1 May 2002Published inissue 1 December...
The readily available 1-phosphino-2-sulfenylferrocenes 1 provide very high enantioselectivities in Pd-catalyzed allylic substitution reactions and alkylative ring opening of 7-oxabenzonorbornadiene with dialkylzinc reagents.
The use of the sulfinyl group as a chiral auxiliary in intermolecular Heck reactions cyclic alkenes with iodoarenes has been studied (see scheme). High asymmetric inductions were obtained by palladium-chelating o-(N,N-dimethylamino)phenylsulfinyl group. Both and double can be performed this auxiliary. final reductive elimination sulfoxide gave 1-aryl-substituted or 1,3-diaryl-substituted compounds high enantiomeric purity. study variety substituted sulfoxides auxiliaries...
ADVERTISEMENT RETURN TO ISSUEPREVCommunicationNEXTA Novel Sulfoxide-Directed Route to Enantiopure Tetrahydrofurans: Application the Expedient Formal Synthesis of (+)-trans-Kumausyne and (+)-Kumausallene1,†Roberto Fernández de la Pradilla, Carlos Montero, Julián Priego, Luis Alfonso Martínez-CruzView Author Information Instituto Química Orgánica, CSIC, Juan Cierva, 3, E-28006 Madrid, Spain, Departamento Cristalografía, Química-Física Rocasolano, Serrano 119, Spain Cite this: J. Org. Chem....
PCA 4233 [2-(phenylthio)ethyl-5-ethoxycarbonyl-2,4,6-trimethyl- 1,4-dihydropyridine-3-carboxylate] and 4248 [2-(phenylthio) ethyl-5-methoxycarbonyl-2, 4, 6-trimethyl-1, 4-dihydropyridine-3-carboxylate], two compounds developed from a series of 1,4-dihydropyridines that lack pharmacologic effects on voltage-operated calcium channels, were found to block selectively rabbit operated human platelet aggregation secretion, binding [3H]-labeled platelet-activating factor (PAF) polymorphonuclear PAF...
The ability of PCA 4248 [2-(phenylthio)ethyl-5-methoxycarbonyl- 2,4,6-trimethyl-1,4-dihydropyridine-3-carboxylate] to block PAF-induced systemic hypotension and protein-rich plasma extravasation in rats, death mice, was tested. These studies were complemented with experiments using soluble aggregates immunoglobulin G (A-IgG), bacterial endotoxin the cytokine tumor necrosis factor as putative inducers generation endogenous PAF. Significant inhibition observed i.v. at doses 0.3 1 mg/kg (IC50...
Treatment of acyclic α-hydroxyalkyl α,β-unsaturated sulfoxides with t-BuOOH/VO(acac)2 results in rapid oxidation to the unsaturated sulfones followed by an unusual regio- and stereoselective epoxidation at sulfones; this methodology has been applied preparation carbohydrate-like fragments.
A new synthetic route to afford 2-amino-5-aryl thiazoles has been developed. The starting aminothiazole derivative can be arylated at position 5 with aryl iodides under palladium-catalyzed conditions. Mechanistic studies suggest a proton-abstraction pathway for this transformation.
Herein we describe a method to orthogonally remove on-DNA N-Cbz, N-Alloc, N-Allyl, O-Bn, and O-Allyl protecting groups in the presence of other common afford free amines carboxylic acids, respectively. The developed uses NaBH4 as source hydrogen Pd(OAc)2 under DNA aqueous conditions. In addition, conditions were able successfully hydrogenate triple double bonds totally saturated compounds. Furthermore, introduce new alternative procedure reduce azides aromatic nitro compounds primary amines.
A ready access to a new family of planar chiral ferrocenes, the (RFc,RS)-2-amino substituted 1-tert-butylsulfinylferrocenes, is described; in case sulfonamide series enantioselectivities up 96% were obtained addition Et2Zn aromatic aldehydes.
The asymmetric Heck reaction of the readily available (R) 1-tert-butylsulfinyl-1-cyclopentene with a variety para- and meta-substituted arenediazonium tetrafluoroborates is described. In presence Ag2CO3 as base, in CH3CN at rt, reactions occur good yields (72-79%) high diastereoselectivities (de = 82-92%) to afford (3S,SR)-3-aryl-2-tert-butylsulfinyl-1-cyclopentenes major adducts. contrast, poor results were obtained from ortho-substituted salts.
ADVERTISEMENT RETURN TO ISSUEPREVCommunicationNEXTStereoselective Nucleophilic Epoxidation of Vinyl Sulfoxides: A Novel Route to Enantiopure Sulfinyl Oxiranes†,1Roberto Fernández de la Pradilla, Sonia Castro, Pilar Manzano, Julián Priego, and Alma VisoView Author Information Instituto Química Orgánica, CSIC, Juan Cierva, 3, 28006 Madrid, Spain, Departamento Orgánica I, Facultad Química, Universidad Complutense, 28040 Spain Cite this: J. Org. Chem. 1996, 61, 11, 3586–3587Publication Date...
The nucleophilic epoxidation of readily available vinyl and dienyl sulfoxides with MOO-t-Bu (M = Li, Na, K) takes place in good yields, complete preservation double bond geometry most cases moderate to excellent diastereofacial selectivity produce enantio- diastereomerically pure α,β-epoxy sulfoxides, valuable synthetic intermediates. Subsequent straightforward oxidation at sulfur affords the corresponding enantiopure sulfonyl oxiranes. For (1E)-2-sulfinyl dienes, facial this novel process...
A novel route to enantiopure densely functionalized epoxy sulfinyl tetrahydrofurans, based on the unexpected and highly stereoselective remote nucleophilic epoxidation of hydroxy 1-sulfinyl butadienes with t-BuOOK, followed by ring closure subsequent resulting dihydrofurans, is described. Alternatively, treatment these dienes m-CPBA acid-catalyzed cyclization gives rise related sulfonyl dihydrofurans in high yields but low selectivity. The stereochemical outcome substrates has also been studied.
Codification of DNA Encoded Libraries (DELs) is critical for successful ligand identification molecules that bind a protein interest (POI). There are different encoding strategies permit, instance, the customization DEL testing single or dual pharmacophores (single strand DNA) producing and screening large diversity libraries small (double DNA). Both approaches challenges, either from synthetic point view, selection methodology to be utilized screening. The Head-Piece contains sequence...
The nucleophilic epoxidation of a variety alpha'-(1-hydroxyalkyl) vinyl sulfones and sulfoxides has been studied. give rise to anti oxiranes with modest (E) or excellent (Z) selectivities in good yields. (E)-sulfoxides display low reactivity within reinforcing/nonreinforcing scenario. use t-BuOOLi Et(2)O allows for highly syn-selective epoxidation-oxidation. (Z)-sulfoxides remarkably high under these conditions. reinforcing (S,S(S)) diastereomers (3e-g) yield hydroxy sulfinyl yields...
The nucleophilic epoxidation of simple (γ-silyloxy)vinyl sulfoxides takes place with complete stereocontrol and high yields. For substrates bearing an additional substituent at the γ position, a reinforcing/nonreinforcing scenario is operative. While E Z silylated undergo primarily sulfur directed good to excellent diastereocontrol, related (E)-(2-methoxyethoxy)methyl ethers display diminished selectivity for diastereomer derived from nonreinforcing scenario.