Gold-Catalyzed Intramolecular Hydroamination of o-Alkynylbenzyl Carbamates: A Route to Chiral Fluorinated Isoindoline and Isoquinoline Derivatives

Enantiomerically pure fluorinated isoindoline and dihydroisoquinoline scaffolds have been prepared through a diastereoselective addition of fluorinated nucleophiles to Ellman’s N-(tert-butanesulfinyl)imines followed by a sequence of Sonogashira cross-coupling/gold(I)-catalyzed cycloisomerization of the corresponding carbamate. A more favored 5-exo-dig mechanism was observed mainly due to an electronic effect of the fluorinated group.

8-Iodonaphthalene-1-carbaldehyde: A Versatile Building Block for Diversity-Oriented Synthesis.

The scarcely studied 8-halonaphthalene-1-carbaldehyde structure has been converted into the corresponding Ellman’s imine and subjected to several transformations, thus achieving an assorted library of polycyclic carbo- and heterocycles. The potential of this scaffold for Diversity-Oriented Synthesis has been shown. Most of these skeletons are unprecedented and, therefore, cover unexplored regions of the chemical space.

Structure-Based Design of an RNA-Bindingp-Terphenylene Scaffold that Inhibits HIV-1 Rev Protein Function

Inside Back Cover: Structure-Based Design of an RNA-Bindingp-Terphenylene Scaffold that Inhibits HIV-1 Rev Protein Function (Angew. Chem. Int. Ed. 50/2013)

ChemInform Abstract: Asymmetric Synthesis of Fluorinated Isoindolinones Through Palladium-Catalyzed Carbonylative Amination of Enantioenriched Benzylic Carbamates.

The asymmetric synthesis of fluorinated isoindolinones has been achieved by a palladium-catalyzed aminocarbonylation reaction of the corresponding α-fluoroalkyl o-iodobenzylamines. A base-mediated anti β-hydride elimination process was suggested to explain the partial erosion of the optical purity observed in some cases. This mechanistic rationale enabled the minimization of this partial racemization by fine-tuning the pKa of the base.

Asymmetric Synthesis of Fluorinated Isoindolinones through Palladium-Catalyzed Carbonylative Amination of Enantioenriched Benzylic Carbamates

The asymmetric synthesis of fluorinated isoindolinones has been achieved by a palladium-catalyzed aminocarbonylation reaction of the corresponding -fluoroalkyl o-iodobenzylamines. A base-mediated anti -hydride elimination process was suggested to explain the partial erosion of the optical purity observed in some cases. This mechanistic rationale enabled the minimization of this partial racemization by fine-tuning the pK(a) of the base.

ChemInform Abstract: Gold-Catalyzed Intramolecular Hydroamination of o-Alkynylbenzyl Carbamates: A Route to Chiral Fluorinated Isoindoline and Isoquinoline Derivatives.

Title compounds are prepared in enantiomerically pure form by the diastereoselective addition of fluorinated nucleophiles to N-(tert-butanesulfinyl)imines (I) followed by a sequence of Sonogashira cross-coupling/gold(I)-catalyzed cycloisomerization of the corresponding carbamate.

Solution versus Fluorous versus Solid-Phase Synthesis of 2,5-Disubstituted 1,3-Azoles. Preliminary Antibacterial Activity Studies

A small library of compounds with an oxa(thia)zole scaffold and structural diversity in both positions 2 and 5 has been synthesized. Double acylation of a protected glycine affords intermediate α-amido-β-ketoesters, which in turn can be dehydrated to afford 1,3-oxazoles or reacted with Lawesson’s reagent to furnish 1,3-thiazoles. This procedure was designed with its adaptation to fluorous techniques in mind. Thus, when a protected glycine with a fluorous tag in the ester moiety is used as a starting material, the synthesis can be easily completed without column chromatography purification of intermediate compounds with good to excellent yields, thus affording a suitable entry to the prepara…

Stress and Psychological Distress in Emerging Adulthood: A Gender Analysis

Emerging adulthood is a critical period of life that entails many life transitions in living arrangements, relationships, education and employment, which can generate stress and psychological distress in the emerging adult. The aim of the present study was to assess the relevance of stress, coping styles, self-esteem and perceived social support in the distress of emerging adult women and men. The sample consists of 4816 people (50% females) from the Spanish general population, ranging in age from 18 to 29 years old. All participants were assessed through questionnaires and scales that assess psychological distress, stress, coping styles, self-esteem and social support. Women scored higher …

Innenrücktitelbild: Structure-Based Design of an RNA-Bindingp-Terphenylene Scaffold that Inhibits HIV-1 Rev Protein Function (Angew. Chem. 50/2013)

ChemInform Abstract: Solution versus Fluorous versus Solid-Phase Synthesis of 2,5-Disubstituted 1,3-Azoles. Preliminary Antibacterial Activity Studies.

A small library of compounds with an oxa(thia)zole scaffold and structural diversity in both positions 2 and 5 has been synthesized. Double acylation of a protected glycine affords intermediate alpha-amido-beta-ketoesters, which in turn can be dehydrated to afford 1,3-oxazoles or reacted with Lawesson's reagent to furnish 1,3-thiazoles. This procedure was designed with its adaptation to fluorous techniques in mind. Thus, when a protected glycine with a fluorous tag in the ester moiety is used as a starting material, the synthesis can be easily completed without column chromatography purification of intermediate compounds with good to excellent yields, thus affording a suitable entry to the …

CCDC 916244: Experimental Crystal Structure Determination

Related Article: Santos Fustero, Ignacio Ibáñez, Pablo Barrio, Miguel A. Maestro, Silvia Catalán|2013|Org.Lett.|15|832|doi:10.1021/ol3035142

CCDC 916245: Experimental Crystal Structure Determination

Related Article: Santos Fustero, Ignacio Ibáñez, Pablo Barrio, Miguel A. Maestro, Silvia Catalán|2013|Org.Lett.|15|832|doi:10.1021/ol3035142