A5031142155- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Asymmetric Synthesis and Catalysis
- Synthetic Organic Chemistry Methods
- Catalytic Alkyne Reactions
- Asymmetric Hydrogenation and Catalysis
- Synthesis and Catalytic Reactions
- Chemical Synthesis and Analysis
- Catalytic C–H Functionalization Methods
- Traditional and Medicinal Uses of Annonaceae
- Crystallography and molecular interactions
- Inorganic and Organometallic Chemistry
- Click Chemistry and Applications
- Gene expression and cancer classification
- Synthesis and Reactions of Organic Compounds
- Chemistry and Chemical Engineering
- Surface Chemistry and Catalysis
- Fluorine in Organic Chemistry
- Cyclopropane Reaction Mechanisms
- Chemical Synthesis and Reactions
- Oxidative Organic Chemistry Reactions
- Carbohydrate Chemistry and Synthesis
University of the Basque Country
2013-2022
University of Bristol
2021
Catalytic and asymmetric Michael reactions constitute very powerful tools for the construction of new C–C bonds in synthesis, but most reports claiming high selectivity are limited to some specific combinations nucleophile/electrophile compound types, only few successful methods deal with generation all-carbon quaternary stereocenters. A contribution solve this gap is presented here based on chiral bifunctional Brønsted base (BB) catalysis use α′-oxy enones as enabling acceptors ambivalent...
A catalytic and highly stereoselective entry to propargylic alcohols products derived thereof is reported based on an unprecedented cross-aldol coupling between unmodified aldehydes ynals. The method requires amine–metal salt–Brønsted acid ternary catalyst system implies synergistic activation of the donor aldehyde via enamine acceptor carbonyl unique reversible metal–alkyne complexation. Specifically, by using a combined α,α-dialkylprolinol silyl ether–CuI–PhCO2H system, remarkably high...
Abstract The catalytic asymmetric synthesis of both α‐substituted and α,α‐disubstituted (quaternary) β‐tetralones through direct α‐functionalization the corresponding β‐tetralone precursor remains elusive. A designed Brønsted base‐squaramide bifunctional catalyst promotes conjugate addition either unsubstituted or α‐monosubstituted to nitroalkenes. Under these reaction conditions, not only enolization, thus functionalization, occurs at α‐carbon atom exclusively, but adducts including...
The selective tagging of amino acids within a peptide framework while using atom-economical C-H counterparts poses an unmet challenge chemistry. Herein, we report novel Pd-catalyzed late-stage acylation collection Tyr-containing peptides with alcohols. This water-compatible labeling technique is distinguished by its reliable scalability and features the use ethanol as renewable feedstock for assembly variety peptidomimetics.
In this study, the unique capacity of bifunctional Brønsted bases to generate α-branched ketone dienolates and control both site- stereoselectivity their addition reactions representative classes carbon electrophiles (i.e., vinyl sulfones, nitroolefins, formaldehyde) is documented. We demonstrate that by using selected chiral tertiary amine/squaramide catalysts, β,γ-unsaturated cycloalkanones proceed through dienolate Cα almost exclusively provide all-carbon quaternary cyclic adducts in good...
Here we report the highly enantio- and syn-selective synthesis of β-hydroxy α-amino acids from glycine imine derivatives under Brønsted base (BB) catalysis. The key this approach is use benzophenone-derived o-nitroanilide as a pronucleophile, where framework provides an efficient hydrogen-bonding platform that accounts for nucleophile reactivity diastereoselectivity.
Abstract A Pd‐catalyzed C(sp 2 )−H acetoxylation of Tyr‐containing peptides is described. The method relies on the use a removable 2‐pyridyloxy group as directing and distinguished by its reliable scalability easily tuned regioselectivity to perform mono‐ diacetoxylation reactions. Remarkably, assembly L–DOPA peptidomimetics beyond reach upon cleavage group.
Abstract The catalytic asymmetric synthesis of both α‐substituted and α,α‐disubstituted (quaternary) β‐tetralones through direct α‐functionalization the corresponding β‐tetralone precursor remains elusive. A designed Brønsted base‐squaramide bifunctional catalyst promotes conjugate addition either unsubstituted or α‐monosubstituted to nitroalkenes. Under these reaction conditions, not only enolization, thus functionalization, occurs at α‐carbon atom exclusively, but adducts including...
Abstract An effective asymmetric route to functionalized 1,6‐ and 1,7‐enynes has been developed based on a direct cross‐aldol reaction between ω‐unsaturated aldehydes propargylic (α,β‐ynals) promoted by combined α,α‐dialkylprolinol ether/Brønsted acid catalysis. This synergistic activation strategy is key accessing the corresponding aldol adducts with high stereoselectivity, both enantio‐ diastereoselectivity. The also proceeds well ketones (α,β‐ynones) thus enabling stereocontrolled access...
l -Tyrosine provides a precursor for practical synthesis of the unstable primary metabolite -arogenate and some stabilised arogenate analogues.
Studies in our group have shown that α'-oxy enones react the presence of Brønsted base catalysts with 3-substituted oxindoles, cyanoesters, 5H-oxazol-4-ones, 1H-imidazol-4-(5H)-ones and azlactones to give corresponding 1,5-dicarbonyl Michael adducts a fully substituted carbon center high enantioselectivity. For example, reaction between 2 enone 1 is efficiently promoted by catalyst C1 led, after desilylation, products 3 good yields ee's. In each case, reactions proceed site selectivity no...
Herein we present an effective asymmetric route to functionalized 1,6- and 1,7- enynes based on a direct cross-aldol reaction between ω-unsaturated aldehydes propargylic (α,β-ynals) promoted by combined α,α-dialkylprolinol ether/Brønsted acid catalysis. This synergistic activation strategy is key access the corresponding aldol adducts with high enantio- diastereoselectivity.[1] The also proceeds well ketones (α,β-ynones) thus enabling stereocontrolled tertiary alcohols. utility of these...
Herein we present a practical and selective route to synthetically usefull propargylic amines alcohols.[1] The key of both approaches is the combined use an α,α-dialkylprolinol ether catalyst Brønsted acid that leads adducts with high levels diastereo- enantiocontrol (anti/syn up 90:10, ee 95%). In aldol addition it was also observed presence CuI as third component, generally provided increase in reaction diastereoselectivity 95:5). This study uncovers new case chiral enamine catalysis which...
Abstract Direct cross‐aldol reaction between ω‐unsaturated aldehydes and propargylic is developed to yield functionalized 1,6‐ 1,7‐enynes the conversion of these products bicyclic cyclopentenone derivatives by Pauson—Khand demonstrated.