Javier Luis Barrera

Universidad del País Vasco / Euskal Herriko Unibertsitatea | UPV/EHU · Organic Chemistry II

Alice points out the preference of one conformational enantiomer by “crossing the mirror” thanks to the catalyst formed from the phosphoric acid and bromine “delivered” by N‐bromosuccinimide (NBS). Both the selected conformer and the new catalyst formed in situ merge their respective roads to converge on the product. More information can be found i...

We have studied the enantioselective transannular aminohalogenation reaction of unsaturated medium‐sized cyclic benzosulfonamides by using both chiral Brønsted acid and phase‐transfer catalysis. Under optimized conditions, a variety of bicyclic adducts can be obtained with good yields and high enantioselectivities. The mechanism of the reaction was...

A transannular approach has been developed for the construction of pyrrolo[1,2-b]isoquinolinones starting from benzo-fused nine-membered enelactams. This process takes place in the presence of a halogenating agent and under Brønsted acid catalysis and proceeds via a transannular amidohalogenation, followed by elimination. The reaction has been foun...

A well-established strategy to synthesize heterogeneous, metal-organic framework (MOF) catalysts that exhibit nanoconfinement effects, and specific pores with highly-localized catalytic sites, is to use organic linkers containing organocatalytic centers. Here, we report that by combining this linker approach with reticular chemistry, and exploiting...

Non-covalent inclusion of small acid and base molecules (CH3COOH and NEt3) in an imine structure based on micrometre COF-300 crystals and amorphous nanoparticles results on the facile modulation of its acid-base properties. Such strategy results in the triggering of acidic/basic catalytic activity of the otherwise inactive materials towards ring-op...

The most useful strategies for the alkylation of allylic systems are related to the Tsuji-Trost reaction or the use of different Lewis acids. Herein we report a photocatalytic approach for the allylation reaction of a variety of nucleophiles, such as heteroarenes, amines and alcohols. This method is compatible with a large variety of pyrroles and i...

Tandem and multicomponent one‐pot reactions are highly attractive because they enable synthesis of target molecules in a single reaction vessel. However, they are difficult to control, as they can lead to the formation of many undesired side‐products. Herein we report the use of metal‐organic framework (MOF) pores decorated with organocatalytic squ...

In this communication, a new visible light photocatalytic strategy for the synthesis of enantioenriched dihydrofuranes and cyclopentenes via an intramolecular nitro-cyclopropane ring expansion reaction is presented. This process takes place under mild conditions with good yields and excellent enantioselectivities in the final products. Moreover, me...

In this communication, a new visible light photocatalytic strategy for the synthesis of enantioenriched dihydrofuranes and cyclopentenes via an intramolecular nitro-cyclopropane ring expansion reaction is presented. This process takes place under mild conditions with good yields and excellent enantioselectivities in the final products. Moreover, me...

A metal‐free synthesis of biologically important benzazepines is achieved through a single synthetic operation involving an oxidative C–H bond functionalization and ring expansion with diazomethanes as key reagent. This represents a new, strong methodology for the straightforward construction of the seven‐ring N‐heterocyclic structures under mild c...

Invited for the cover of this issue is the group of José Alemán at the University Autónoma of Madrid. The image depicts how the right temperature is important for organocatalytic processes and Spanish wine. Read the full text of the article at 10.1002/chem.201603437.

The Spanish tapas and wines are well known worldwide for their culinary qualities. Just as the choice and the temperature of the wine are crucial for the good taste of the La Mancha cheese or Spanish ham, the choice of catalyst and reaction temperature are crucial for obtaining the desired product in an organocatalytic process. The Ribera del Duero...

A highly diastereoselective synthesis of trisubstituted Z- or E-enals, which are important intermediates in organic synthesis, as well as being present in natural products, is described using different alkynals and nucleophiles as starting materials. Diastereocontrol is mainly governed by the appropriate catalyst. Therefore, those reactions control...

Cyclopropanes with a quaternary center are efficiently synthesized starting from bromonitroalkenes and alkyl aldehydes under aminocatalysis, giving good yield, excellent enantioselectivities, and moderate to excellent diastereoselectivities. This work is a novel approach using bromonitroalkenes as starting material instead of the usual synthesis wi...

In this work, we describe the 1,4-Michael addition of the 1,3-dicarbonyl compounds to activated ethylenes under st-DNA catalysis in water. The reaction of the β-ketoester 4 with nitroolefins and conjugated carbonyls proceeds quite well, whereas other less activated ethylenes exhibit low or null reactivity. The catalyst can be recovered and reused f...