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1. Identification of 1,3-Diiminoisoindoline Carbohydrazides as Potential Antimalarial Candidates

Author

W. Bernd Schweizer, François Diederich, Isabella Siepe, Markus Fischer, Anthoni W. van Zijl, Céline Freymond, Marcel Kaiser, Matthias Rottmann, Victoria Illarionova, Franz Röhl, Paolo Mombelli, Julie G. Geist, Reto Brun, and Matthias Witschel

Subjects
Cell Survival, Stereochemistry, Plasmodium falciparum, Isoindoles, Carbohydrazide, 01 natural sciences, Biochemistry, Cell Line, Antimalarials, Structure-Activity Relationship, 03 medical and health sciences, chemistry.chemical_compound, Drug Discovery, Humans, Structure–activity relationship, Malaria, Falciparum, General Pharmacology, Toxicology and Pharmaceutics, Cytotoxicity, Cell survival, 030304 developmental biology, Pharmacology, chemistry.chemical_classification, 0303 health sciences, biology, 010405 organic chemistry, Organic Chemistry, Biological activity, biology.organism_classification, 0104 chemical sciences, 3. Good health, Hydrazines, Enzyme, chemistry, Cell culture, Molecular Medicine
Abstract

A series of inhibitors of plant enzymes of the non-mevalonate pathway from herbicide research efforts at BASF were screened for antimalarial activity in a cell-based assay. A 1,3-diiminoisoindoline carbohydrazide was found to inhibit the growth of Plasmodium falciparum with an IC(50) value

Published
2011

2. Catalytic Enantioselective Synthesis of Vicinal Dialkyl Arrays

Author

Ben L. Feringa, Anthoni W. van Zijl, Ferrnando Lopez, Wiktor Szymanski, Adriaan J. Minnaard, Stratingh Institute of Chemistry, Synthetic Organic Chemistry, Biotechnology, and Chemical Biology 2

Subjects
LASIUS-MERIDIONALIS, Ketone, Alkylation, Stereochemistry, Molecular Conformation, Chemical synthesis, Catalysis, Pheromones, Tsuji–Trost reaction, Animals, Sulfhydryl Compounds, GRIGNARD-REAGENTS, ALLYLIC SUBSTITUTION-REACTIONS, chemistry.chemical_classification, Aldehydes, Addition reaction, PHARAOHS ANT, Ants, Chemistry, Organic Chemistry, Enantioselective synthesis, Esters, Stereoisomerism, TRAIL PHEROMONE, Ketones, ASYMMETRIC CONJUGATE ADDITION, OLEFIN CROSS-METATHESIS, STEREOSELECTIVE-SYNTHESIS, Alcohols, Stereoselectivity, MYCOBACTERIUM-TUBERCULOSIS, MANDIBULAR GLAND SECRETION, Copper, Vicinal
Abstract

With a consecutive "asymmetric allylic alkylation (AAA)/cross-metathesis (CM)/conjugate addition (CA)" protocol it is possible to synthesize either stereoisomer of compounds containing a vicinal dialkyl array with excellent stereoselectivity. The versatility of this protocol in natural product synthesis is demonstrated in the preparation of the ant pheromones faranal and lasiol.

Published
2008

3. Highly enantioselective copper-catalyzed allylic alkylation with phosphoramidite ligands

Author

Leggy A. Arnold, Adriaan J. Minnaard, Anthoni W. van Zijl, Ben L. Feringa, and Synthetic Organic Chemistry

Subjects
inorganic chemicals, allylic alkylation, Allylic rearrangement, chemistry.chemical_element, diorganozinc compounds, Catalysis, Tsuji–Trost reaction, PALLADIUM COMPLEX, polycyclic compounds, Organic chemistry, heterocyclic compounds, GRIGNARD-REAGENTS, CONJUGATE ADDITION, ACETATES, Phosphoramidite, organic chemicals, Enantioselective synthesis, CHIRAL LIGANDS, Regioselectivity, food and beverages, asymmetric catalysis, SUBSTITUTION, REGIOSELECTIVITY, General Chemistry, phosphoramidite ligands, Copper, PHOSPHORUS AMIDITES, chemistry, Reagent, copper, ORGANOZINC REAGENTS, S(N)2 '-substitution
Abstract

New phosphoramidites were applied as chiral ligands in the Cu-catalyzed allylic alkylation with dialkylzinc reagents. A variety of substrates, reagents and chiral ligands were screened, resulting in improved catalytic methodology for allylic bromides in which enantioselectivities up to 88% were reached.

Published
2004

4. Highly enantioselective Cu-catalysed allylic substitutions with Grignard reagents

Author

Anthoni W. van Zijl, Fernando López, Ben L. Feringa, Adriaan J. Minnaard, Molecular Inorganic Chemistry, Stratingh Institute of Chemistry, Synthetic Organic Chemistry, and Chemical Biology 2

Subjects
Allylic rearrangement, Chemistry, Metals and Alloys, Enantioselective synthesis, ESTERS, EFFICIENT, General Chemistry, Alkylation, ASYMMETRIC CONJUGATE ADDITION, ALKYLATION, Catalysis, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, AMINATION, PHOSPHORAMIDITE LIGANDS, Reagent, Materials Chemistry, Ceramics and Composites, Organic chemistry, COMPLEXES, ENONES, Amination
Abstract

A catalyst system able to perform highly enantioselective Cu-catalysed allylic alkylations with Grignard reagents is described.

Published
2006

5. ChemInform Abstract: Catalytic Asymmetric Synthesis of Chromenes and Tetrahydroquinolines via Sequential Allylic Alkylation and Intramolecular Heck Coupling

Author

Valentin Hornillos, Bernard Feringa, and Anthoni W. van Zijl

Subjects
Allylic rearrangement, Tsuji–Trost reaction, Chemistry, Reagent, Intramolecular force, Heck reaction, Enantioselective synthesis, General Medicine, Combinatorial chemistry, Catalysis
Abstract

Highly enantioselective synthesis of title compounds (IV) is achieved by combining asymmetric Cu-catalyzed allylic substitution with Grignard reagents (II) and intramolecular Heck reaction.

Published
2012

6. Catalytic asymmetric synthesis of chromenes and tetrahydroquinolines via sequential allylic alkylation and intramolecular Heck coupling

Author

Valentin Hornillos, Bernard Feringa, Anthoni W. van Zijl, Stratingh Institute of Chemistry, and Synthetic Organic Chemistry

Subjects
Bromides, Allylic rearrangement, Double bond, Alkylation, Catalysis, METATHESIS, Tsuji–Trost reaction, Heck reaction, Materials Chemistry, Organic chemistry, Benzopyrans, GRIGNARD-REAGENTS, CONJUGATE ADDITION, chemistry.chemical_classification, Chemistry, Metals and Alloys, Enantioselective synthesis, Stereoisomerism, General Chemistry, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, Hydroboration, Intramolecular force, Ceramics and Composites, Quinolines, Copper, HETEROCYCLES, BUILDING-BLOCKS
Abstract

Highly enantioselective synthesis of chiral chromenes and tetra-hydroquinolines is achieved by combining asymmetric copper-catalyzed allylic substitution with Grignard reagents and an efficient intramolecular Heck reaction. Moreover, the exocyclic double bond formed in the cyclisation was subjected to RCM, hydroboration and hydrogenation illuminating the synthetic versatility of these heterocycles.

Published
2012

7. ChemInform Abstract: Catalytic Enantioselective Synthesis of Naturally Occurring Butenolides via hetero-Allylic Alkylation and Ring Closing Metathesis

Author

Bernard Feringa, Martín Fañanás-Mastral, Anthoni W. van Zijl, Koen Geurts, Stephen P. Fletcher, Adriaan J. Minnaard, and Bin Mao

Subjects
chemistry.chemical_classification, Tsuji–Trost reaction, Ring-closing metathesis, Chemistry, Stereochemistry, Enantioselective synthesis, General Medicine, Alkylation, Lactone, Catalysis
Abstract

An efficient catalytic asymmetric synthesis of chiral γ-butenolides was developed based on the hetero-allylic asymmetric alkylation (h-AAA) in combination with ring closing metathesis (RCM). The synthetic potential of the h-AAA-RCM protocol was illustrated with the facile synthesis of (-)-whiskey lactone, (-)-cognac lactone, (-)-nephrosteranic acid, and (-)-roccellaric acid.

Published
2011

8. ChemInform Abstract: Asymmetric Allylic Alkylation in Combination with Ring-Closing Metathesis for the Preparation of Chiral N-Heterocycles

Author

Johannes F. Teichert, Bernard Feringa, Anthoni W. van Zijl, Suyan Zhang, Jan Willem Slaa, and Adriaan J. Minnaard

Subjects
Tsuji–Trost reaction, Allylic rearrangement, chemistry.chemical_compound, Ring-closing metathesis, chemistry, Olefin metathesis, Bromide, General Medicine, Metathesis, Medicinal chemistry
Abstract

Asymmetric copper-catalyzed allylic substitution with methylmagnesium bromide is employed in combination with ring-closing olefin metathesis or ene-yne metathesis to achieve the synthesis of chiral, unsaturated nitrogen heterocycles. The resulting six- to eight-membered chiral heterocycles are accessible in high yields and with excellent enantioselectivities.

Published
2011

9. Catalytic Enantioselective Synthesis of Naturally Occurring Butenolides via Hetero-Allylic Alkylation and Ring Closing Metathesis

Author

Koen Geurts, Stephen P. Fletcher, Martín Fañanás-Mastral, Adriaan J. Minnaard, Anthoni W. van Zijl, Bernard Feringa, Bin Mao, Faculty of Science and Engineering, Stratingh Institute of Chemistry, Synthetic Organic Chemistry, and Chemical Biology 2

Subjects
PARACONIC ACIDS, Alkylation, Stereochemistry, Allyl compound, Stereoisomerism, ASYMMETRIC DIHYDROXYLATION, Biochemistry, Catalysis, Tsuji–Trost reaction, Ring-closing metathesis, 4-Butyrolactone, (-)-ROCCELLARIC ACID, (+)-TRANS-WHISKEY LACTONE, Physical and Theoretical Chemistry, Furans, chemistry.chemical_classification, Biological Products, Molecular Structure, GAMMA-LACTONES, Organic Chemistry, Enantioselective synthesis, (+)-NEPHROSTERANIC ACID, (+)-ROCCELLARIC ACID, TRANS-WHISKEY LACTONE, Allyl Compounds, (+)-TRANS-COGNAC LACTONE, chemistry, (-)-NEPHROSTERANIC ACID, Lactone
Abstract

An efficient catalytic asymmetric synthesis of chiral γ-butenolides was developed based on the hetero-allylic asymmetric alkylation (h-AAA) in combination with ring closing metathesis (RCM). The synthetic potential of the h-AAA-RCM protocol was illustrated with the facile synthesis of (-)-whiskey lactone, (-)-cognac lactone, (-)-nephrosteranic acid, and (-)-roccellaric acid.

Published
2011

13. Straightforward synthesis of alpha,beta-unsaturated thioesters via ruthenium-catalyzed olefin cross-metathesis with thioacrylate

Author

Adriaan J. Minnaard, Anthoni W. van Zijl, Ben L. Feringa, Synthetic Organic Chemistry, and Chemical Biology 2

Subjects
inorganic chemicals, THIOL ESTERS, KETONE SYNTHESIS, chemistry.chemical_element, Metathesis, Thioester, ALDOL CONDENSATIONS, Chemical synthesis, Catalysis, chemistry.chemical_compound, Organic chemistry, GRIGNARD-REAGENTS, CONJUGATE ADDITION, ASYMMETRIC-SYNTHESIS, chemistry.chemical_classification, Olefin fiber, Chemistry, organic chemicals, Organic Chemistry, Enantioselective synthesis, Ruthenium, SILYL ENOL ETHERS, STEREOSELECTIVE-SYNTHESIS, ACID, Organic synthesis, MYCOBACTERIUM-TUBERCULOSIS
Abstract

The cross-metathesis reaction of S-ethyl thioacrylate with a variety of olefins is effectively catalyzed by using a ruthenium benzylidene olefin metathesis catalyst. This reaction provides a convenient and versatile route to substituted alpha,beta-unsaturated thioesters, key building blocks in organic synthesis.

Published
2008

14. Synthesis of Optically Active Bifunctional Building Blocks Through Enantioselective Copper-Catalyzed Allylic Alkylation Using Grignard Reagents

Author

Ben L. Feringa, Anthoni W. van Zijl, Adriaan J. Minnaard, Fernando López, Molecular Inorganic Chemistry, and Synthetic Organic Chemistry

Subjects
Bromides, Allylic rearrangement, Alkylation, EFFICIENT, ALLYLATION, Hydroxylation, Catalysis, chemistry.chemical_compound, Tsuji–Trost reaction, ASYMMETRIC CATALYSIS, Organic chemistry, Moiety, HYDROGENATION, Amines, Amino Acids, CONJUGATE ADDITION, Bifunctional, Racemization, Substitution reaction, Olefin fiber, Molecular Structure, organic chemicals, Organic Chemistry, ESTERS, Enantioselective synthesis, food and beverages, Stereoisomerism, General Medicine, Combinatorial chemistry, SUBSTITUTION-REACTIONS, PHOSPHORAMIDITE LIGANDS, chemistry, Functional group, COMPLEXES, BETA(2)-AMINO ACIDS, Copper
Abstract

Enantioselective copper-catalyzed allylic alkylations were performed on allylic bromides with a protected hydroxyl or amine functional group using several Grignard reagents and Taniaphos L1 as a ligand. The terminal olefin moiety in the products was transformed into various functional groups without racemization, providing facile access to a variety of versatile bifunctional chiral building blocks.

Published
2007

17. Copper-catalyzed asymmetric allylic substitution reactions with organozinc and Grignard reagents.

Author

Koen Geurts, Stephen P. Fletcher, Anthoni W. van Zijl, Adriaan J. Minnaard, and Ben L. Feringa

Subjects
CONFERENCES & conventions, ORGANIC compounds
Abstract

Paper based on a presentation at the 14th International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-14), 2-6 August 2007, Nara, Japan. Other presentations are published in this issue, pp. 807-1194Asymmetric allylic alkylations (AAAs) are among the most powerful C-C bond-forming reactions. We present a brief overview of copper-catalyzed AAAs with organometallic reagents and discuss our own contributions to this field. Work with zinc reagents and phosphoramidite ligands provided a framework for later developments which employ Grignard reagents and ferrocenyl ligands. High yields and excellent regioselectivities and enantioselectivities are achieved. The AAAs may be more general than previously envisioned, in terms of using substrates functionalized with heteroatoms at various positions; heteroatom substituents at the γ-position provide densely functionalized building blocks. These h-AAA reactions rely on the design of appropriate substrates containing heteroatoms and have allowed us to demonstrate viable new approaches toward the synthesis of versatile organic building blocks. We illustrate that the chiral secondary allylic alcohols, primary homo-allylic alcohols and amines can readily be obtained in high enantiomeric purity in a catalytic asymmetric fashion by copper-catalyzed AAAs. Furthermore, we show that manipulation of the terminal olefin provides chiral building blocks where the ee of the starting materials is preserved. [ABSTRACT FROM AUTHOR]

Published
2008
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