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Cordova, Armando
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Publications (10 of 63) Show all publications
Cordova, A., Afewerki, S., Alimohammadzadeh, R., Sanhueza, I., Tai, C.-W., Osong, S. H., . . . Ibrahem, I. (2019). A sustainable strategy for production and functionalization of nanocelluloses. Pure and Applied Chemistry, 91(5), 865-874
Open this publication in new window or tab >>A sustainable strategy for production and functionalization of nanocelluloses
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2019 (English)In: Pure and Applied Chemistry, ISSN 0033-4545, E-ISSN 1365-3075, Vol. 91, no 5, p. 865-874Article in journal (Refereed) Published
Abstract [en]

A sustainable strategy for the neat production and surface functionalization of nanocellulose from wood pulp is disclosed. It is based on the combination of organocatalysis and click chemistry ("organoclick" chemistry) and starts with nanocellulose production by organic acid catalyzed hydrolysis and esterification of the pulp under neat conditions followed by homogenization. This nanocellulose fabrication route is scalable, reduces energy consumption and the organic acid can be efficiently recycled. Next, the surface is catalytically engineered by "organoclick" chemistry, which allows for selective and versatile attachment of different organic molecules (e.g. fluorescent probes, catalyst and pharmaceuticals). It also enables binding of metal ions and nanoparticles. This was exemplified by the fabrication of a heterogeneous nanocellulose-palladium nanoparticle catalyst, which is used for Suzuki cross-coupling transformations in water. The disclosed surface functionalization methodology is broad in scope and applicable to different nanocelluloses and cellulose based materials as well.

Keywords
click chemistry, cross-coupling reaction, heterogeneous catalysis, nanocellulose, NICE-2016, organocatalysis, surface engineering
National Category
Chemical Engineering
Identifiers
urn:nbn:se:miun:diva-35142 (URN)10.1515/pac-2018-0204 (DOI)000466859500008 ()2-s2.0-85056591870 (Scopus ID)
Available from: 2018-12-10 Created: 2018-12-10 Last updated: 2020-01-21Bibliographically approved
Zhang, K., Deiana, L., Svensson Grape, E., Inge, A. K. & Córdova, A. (2019). Catalytic Enantioselective Synthesis of Bicyclic Lactam N,S-Acetals in One Pot by Cascade Transformations. European Journal of Organic Chemistry, 2019(29), 4649-4657
Open this publication in new window or tab >>Catalytic Enantioselective Synthesis of Bicyclic Lactam N,S-Acetals in One Pot by Cascade Transformations
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2019 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2019, no 29, p. 4649-4657Article in journal (Refereed) Published
Abstract [en]

A versatile strategy for the enantioselective synthesis of bicyclic lactam N,S-acetals by one-pot cascade transformations is disclosed. The transformation of readily available substrates is promoted by chiral amines and creates bicyclic or tricyclic lactam N,S-acetals with high chemo- and stereoselectivity (up to > 99.5:0.5 dr and > 99 % ee) in one-pot operations.

Keywords
Acetals, Asymmetric catalysis, Lactams, Multicomponent reactions, Synthetic methods
Identifiers
urn:nbn:se:miun:diva-36896 (URN)10.1002/ejoc.201900923 (DOI)000479612000001 ()2-s2.0-85070108110 (Scopus ID)
Available from: 2019-08-20 Created: 2019-08-20 Last updated: 2019-09-02Bibliographically approved
Alimohammadzadeh, R., Osong, S. H., Abbaszad Rafi, A., Dahlström, C. & Cordova, A. (2019). Cellulosic Materials: Sustainable Surface Engineering of Lignocellulose and Cellulose by Synergistic Combination of Metal-Free Catalysis and Polyelectrolyte Complexes. Global Challenges, 3(7), Article ID 1970071.
Open this publication in new window or tab >>Cellulosic Materials: Sustainable Surface Engineering of Lignocellulose and Cellulose by Synergistic Combination of Metal-Free Catalysis and Polyelectrolyte Complexes
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2019 (English)In: Global Challenges, ISSN 2056-6646, Vol. 3, no 7, article id 1970071Article in journal (Refereed) Published
Abstract [en]

In article number 1900018 by Armando Cordova and co‐workers, the novel combination of metal‐free catalysis and renewable polyelectrolyte complexes leads to synergistic surface engineering of lignocellulose and cellulose fibers derived from wood. This sustainable strategy allows for improvement and introduction of important properties such as strength (up to 100% in Z‐strength), water resistance, and fluorescence to the renewable fibers and cellulosic materials under eco‐friendly conditions.

National Category
Chemical Engineering
Identifiers
urn:nbn:se:miun:diva-37903 (URN)10.1002/gch2.201970071 (DOI)
Available from: 2019-12-06 Created: 2019-12-06 Last updated: 2019-12-06Bibliographically approved
Afewerki, S. & Córdova, A. (2019). Enamine/Transition Metal Combined Catalysis: Catalytic Transformations Involving Organometallic Electrophilic Intermediates. Topics in Current Chemistry, 377(6), Article ID 38.
Open this publication in new window or tab >>Enamine/Transition Metal Combined Catalysis: Catalytic Transformations Involving Organometallic Electrophilic Intermediates
2019 (English)In: Topics in Current Chemistry, ISSN 2365-0869, Vol. 377, no 6, article id 38Article in journal (Refereed) Published
Abstract [en]

The concept of merging enamine activation catalysis with transition metal catalysis is an important strategy, which allows for selective chemical transformations not accessible without this combination. The amine catalyst activates the carbonyl compounds through the formation of a reactive nucleophilic enamine intermediate and, in parallel, the transition metal activates a wide range of functionalities such as allylic substrates through the formation of reactive electrophilic π-allyl-metal complex. Since the first report of this strategy in 2006, considerable effort has been devoted to the successful advancement of this technology. In this chapter, these findings are highlighted and discussed. 

Keywords
Amino catalysis, Combined catalysis, Enamine catalysis, Organocatalysis, Transition metal catalysis
National Category
Chemical Sciences
Identifiers
urn:nbn:se:miun:diva-38184 (URN)10.1007/s41061-019-0267-y (DOI)000496659200001 ()31732819 (PubMedID)2-s2.0-85075114368 (Scopus ID)
Note

This article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/)

Available from: 2020-01-08 Created: 2020-01-08 Last updated: 2020-01-16Bibliographically approved
Alimohammadzadeh, R., Osong, S. H., Abbaszad Rafi, A., Dahlström, C. & Cordova, A. (2019). Sustainable Surface Engineering of Lignocellulose and Cellulose by Synergistic Combination of Metal‐Free Catalysis and Polyelectrolyte Complexes. Global Challenges, 3, Article ID 1900018.
Open this publication in new window or tab >>Sustainable Surface Engineering of Lignocellulose and Cellulose by Synergistic Combination of Metal‐Free Catalysis and Polyelectrolyte Complexes
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2019 (English)In: Global Challenges, E-ISSN 2056-6646, Vol. 3, article id 1900018Article in journal (Refereed) Published
Abstract [en]

A sustainable strategy for synergistic surface engineering of lignocellulose and cellulose fibers derived from wood by synergistic combination of metal‐free catalysis and renewable polyelectrolyte (PE) complexes is disclosed. The strategy allows for improvement and introduction of important properties such as strength, water resistance, and fluorescence to the renewable fibers and cellulosic materials. For example, the “green” surface engineering significantly increases the strength properties (up to 100% in Z‐strength) of chemi‐thermomechanical pulp (CTMP) and bleached sulphite pulp (BSP)‐derived sheets. Next, performing an organocatalytic silylation with a nontoxic organic acid makes the corresponding lignocellulose and cellulose sheets hydrophobic. A selective color modification of polysaccharides is developed by combining metal‐free catalysis and thiol‐ene click chemistry. Next, fluorescent PE complexes based on cationic starch (CS) and carboxymethylcellulose (CMC) are prepared and used for modification of CTMP or BSP in the presence of a metal‐free catalyst. Laser‐scanning confocal microscopy reveals that the PE‐strength additive is evenly distributed on the CTMP and heterogeneously on the BSP. The fluorescent CS distribution on the CTMP follows the lignin distribution of the lignocellulosic fibers.

Keywords
click chemistry, lignocellulose, metal‐free catalysis, selective fluorescent labeling, sustainable polyelectrolyte complex, synergistic surface engineering, water repellent
National Category
Materials Chemistry Organic Chemistry Paper, Pulp and Fiber Technology
Identifiers
urn:nbn:se:miun:diva-37905 (URN)10.1002/gch2.201900018 (DOI)
Available from: 2019-12-06 Created: 2019-12-06 Last updated: 2019-12-11Bibliographically approved
Afewerki, S., Wang, J.-X. -., Liao, W.-W. -. & Cordova, A. (2019). The Chemical Synthesis and Applications of Tropane Alkaloids. Alkaloids: Chemistry and Biology, 81, 151-233
Open this publication in new window or tab >>The Chemical Synthesis and Applications of Tropane Alkaloids
2019 (English)In: Alkaloids: Chemistry and Biology, ISSN 1099-4831, Vol. 81, p. 151-233Article in journal (Refereed) Published
Abstract [en]

Tropanes are an important class of alkaloid natural products that are found in plants all over the world. These compounds can exhibit significant biological activity and are among the oldest known medicines. In the early 19th century, tropanes were isolated, characterized, and synthesized by notable chemical researchers. Their significant biological activities have inspired tremendous research efforts toward their synthesis and the elucidation of their pharmacological activity both in academia and in industry. In this chapter, which addresses the developments in this field since 1994, the focus is on the synthesis of these compounds, and several examples of sophisticated synthetic protocols involving both asymmetric and catalytic approaches are described. In addition, the structures of more than 100 new alkaloids are included as well as the applications and pharmacological properties of some tropane alkaloids. 

Keywords
Asymmetric synthesis, Biological activity, Catalysis, Cocaine, Total synthesis, Tropane alkaloids
National Category
Chemical Sciences
Identifiers
urn:nbn:se:miun:diva-34595 (URN)10.1016/bs.alkal.2018.06.001 (DOI)
Available from: 2018-10-03 Created: 2018-10-03 Last updated: 2019-01-30Bibliographically approved
Jiang, Y., Deiana, L., Zhang, K., Lin, S. & Córdova, A. (2019). Total Asymmetric Synthesis of Quinine, Quinidine, and Analogues via Catalytic Enantioselective Cascade Transformations. European Journal of Organic Chemistry (35), 6016-6023
Open this publication in new window or tab >>Total Asymmetric Synthesis of Quinine, Quinidine, and Analogues via Catalytic Enantioselective Cascade Transformations
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2019 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 35, p. 6016-6023Article in journal (Refereed) Published
Abstract [en]

A catalytic asymmetric strategy for the total synthesis of quinuclidine natural products, which includes the completed enantioselective synthesis of the classical targets quinine and quinidine is disclosed. It is based on catalytic asymmetric cascade transformations, which paves the road for the synthesis of both enantiomers of the crucial C4 stereocenter with high enantioselectivity (up to 99 % ee) in one pot. Next, developing a route to all possible stereoisomers of a common early-stage intermediate sets the stage for the total synthesis of different enantiomers or epimers of quinine, quinidine and analogues with high selectivity. 

Keywords
Asymmetric catalysis, Cinchona alkaloids, Enantioselectivity, Quinidine, Total synthesis
National Category
Chemical Engineering
Identifiers
urn:nbn:se:miun:diva-37014 (URN)10.1002/ejoc.201901003 (DOI)000482413000001 ()2-s2.0-85070879892 (Scopus ID)
Available from: 2019-09-02 Created: 2019-09-02 Last updated: 2019-10-16Bibliographically approved
Jiang, Y., Deiana, L., Alimohammadzadeh, R., Liu, L., Sun, J. & Córdova, A. (2018). Highly Diastereo- and Enantioselective Cascade Synthesis of Bicyclic Lactams in One-Pot. European Journal of Organic Chemistry, 2018(9), 1158-1164
Open this publication in new window or tab >>Highly Diastereo- and Enantioselective Cascade Synthesis of Bicyclic Lactams in One-Pot
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2018 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2018, no 9, p. 1158-1164Article in journal (Refereed) Published
Abstract [en]

A versatile and highly stereoselective synthetic route to functionalized bi- and tricyclic lactams (up to > 20:1 dr and 99 % ee) in one pot from simple starting materials (allylic alcohols, enals, diamines and amino alcohols) using cascade transformations promoted by chiral amine/Brønsted or metal/chiral amine/Brønsted relay catalysis is disclosed. Here molecular oxygen is employed as the terminal oxidant for the latter relay catalysis approach. 

Keywords
Aminal, Asymmetric catalysis, Bicyclic lactams, Hemiaminal ether, Relay catalysis
National Category
Organic Chemistry
Identifiers
urn:nbn:se:miun:diva-33305 (URN)10.1002/ejoc.201701789 (DOI)000426771400009 ()2-s2.0-85043233373 (Scopus ID)
Available from: 2018-03-19 Created: 2018-03-19 Last updated: 2018-12-11Bibliographically approved
Alimohammadzadeh, R., Osong, S. H., Dahlström, C. & Cordova, A. (2018). Scalable Improvement of the Strength Properties of Chemimechanical Pulp Fibers by Eco-Friendly Catalysis. In: IMPC 2018: . Paper presented at International Mechanical Pulping Conference (IMPC) 2018, May 27-30, 2018, Trondheim, Norway. Trondheim, Norway
Open this publication in new window or tab >>Scalable Improvement of the Strength Properties of Chemimechanical Pulp Fibers by Eco-Friendly Catalysis
2018 (English)In: IMPC 2018, Trondheim, Norway, 2018Conference paper, Published paper (Refereed)
Abstract [en]

The sustainable improvement of the strength properties of chemimechanical pulp by eco-friendlycatalysis is disclosed. Significant research activities have been performed on the use of cationic starchand polyelectrolyte complexes for improving the strength properties of cellulose-based materials. Herewe apply an eco-friendly strategy based on catalysis for significantly improving the strength propertiesof sheets made from chemimechanical pulp (CTMP) and bleeched sulphite pulp (BSP) using sustainablepolyelectrolyte complexes as the strength additives and organocatalysis. This surface engineeringstrategy significantly increased the strength properties of the assembled sheets (up to 100% in the caseof Z-strength). We also developed a catalytic selective colour marking of the cationic potato starch (CS)and carboxymethylcellulose (CMC) in order to elucidated how the specific strength additives aredistributed on the sheets. It revealed that the strength additives were more evenly distributed on thesheets made from CTMP as compared to BSP sheets. This is most likely attributed to the presence oflignin in the former lignocellulosic material. It also contributes to the increase in strength (up to 100%,Z-strength) for the CTMP derived sheets. The selective colour marking method also revealed that morestrength additives had been bound to the pulps in the presence of the catalyst.

Place, publisher, year, edition, pages
Trondheim, Norway: , 2018
National Category
Paper, Pulp and Fiber Technology
Identifiers
urn:nbn:se:miun:diva-34682 (URN)
Conference
International Mechanical Pulping Conference (IMPC) 2018, May 27-30, 2018, Trondheim, Norway
Available from: 2018-10-08 Created: 2018-10-08 Last updated: 2018-10-08Bibliographically approved
Afewerki, S. & Cordova, A. (2017). Cooperative Lewis Acids and Aminocatalysis. In: J. Mlynarski (Ed.), Chiral Lewis Acids in Organic Synthesis: (pp. 345-374). Wiley-Blackwell
Open this publication in new window or tab >>Cooperative Lewis Acids and Aminocatalysis
2017 (English)In: Chiral Lewis Acids in Organic Synthesis / [ed] J. Mlynarski, Wiley-Blackwell , 2017, p. 345-374Chapter in book (Refereed)
Abstract [en]

This chapter describes the cooperative strategy of combining metal catalyst activation with aminocatalysis, with a focus on the metal acting as a Lewis acid catalyst. It gives examples where the metal catalyst promotes the reactivity of different substrates by the formation of reactive intermediates. These intermediates can act either as electrophiles or nucleophiles, which in turn can couple with nucleophilic enamine or electrophilic iminium intermediates formed between the carbonyl compounds and aminocatalyst. The chemical transformation ensues via the merging of the enamine and π‐allyl‐Pd complex via asymmetric counteranion‐direct catalysis (ACDC). Subsequently, several groups reported different co‐catalytic systems and chemical strategies for the α‐allylic alkylation of aldehydes and ketones. Cordova and coworkers reported the first example where iminium activation catalysis is combined with metal catalyst activation cooperatively. The stratagem was demonstrated for the catalytic enantioselective conjugate silyl addition to α,β‐unsaturated aldehydes.

Place, publisher, year, edition, pages
Wiley-Blackwell, 2017
Keywords
α-allylic alkylation, aldehydes, aminocatalysis, asymmetric counteranion-direct catalysis, cooperative Lewis acids, electrophilic iminium, ketones, metal catalyst activation, nucleophilic enamine
National Category
Chemical Engineering
Identifiers
urn:nbn:se:miun:diva-33342 (URN)10.1002/9783527802142.ch10 (DOI)
Available from: 2018-03-22 Created: 2018-03-22 Last updated: 2018-03-22Bibliographically approved
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