New olefin metathesis catalysts bearing polyether clamp in N-heterocyclic carbenes ligands

Hryniewicka, Agnieszka; Misztalewska, Iwona; Czajkowska-Szczykowska, Dorota; Urbańczyk‐Lipkowska, Zofia; Morzycki, Jacek W.; Witkowski, Stanisław

doi:10.1016/j.tet.2014.07.056

Cited by 14 publications

(8 citation statements)

References 45 publications

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“…To a solution of 2,2,5,7,8-pentamethylchromanyl-6-amine ( 12 , 500 mg, 2.3 mmol) in ethanol (96%, 20 mL), 2,3-dihydroxy-1,4-dioxane (138 mg, 1.15 mmol) and two drops of formic acid were added in a manner similar to a that described in [ 40 ]. The reaction mixture was stirred for 24 h. A yellow precipitate appeared.…”

Section: Methodsmentioning

confidence: 99%

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New metathesis catalyst bearing chromanyl moieties at the N-heterocyclic carbene ligand

Hryniewicka¹,

Suchodolski²,

Wojtkielewicz³

et al. 2015

Beilstein J. Org. Chem.

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SummaryThe synthesis of a new type of Hoveyda–Grubbs 2nd generation catalyst bearing a modified N-heterocyclic carbene ligands is reported. The new catalyst contains an NHC ligand symmetrically substituted with chromanyl moieties. The complex was tested in model CM and RCM reactions. It showed very high activity in CM reactions with electron-deficient α,β-unsaturated compounds even at 0 °C. It was also examined in more demanding systems such as conjugated dienes and polyenes. The catalyst is stable, storable and easy to purify.

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Section: Methodsmentioning

confidence: 99%

“…To a solution of ethylenediamine 13 (200 mg, 0.43 mmol) in trimethyl orthoformate (5 mL), ammonium chloride (35 mg, 0.65 mmol) was added in a similar manner as described in [ 40 ]. The reaction mixture was refluxed for 2 h. Solids were filtered off and the filtrate was evaporated to dryness.…”

Section: Methodsmentioning

confidence: 99%

New metathesis catalyst bearing chromanyl moieties at the N-heterocyclic carbene ligand

Hryniewicka¹,

Suchodolski²,

Wojtkielewicz³

et al. 2015

Beilstein J. Org. Chem.

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“…New modified ruthenium metathesis catalystwith polyether clamp embracing N,N'-2,4-dimethylphenyl substituents in the NHC ligand. [27] Scheme6.CM reaction between phenyl vinyl ketone(3)and 1-phenylbut-3-en-1-ol (2). Reagents andconditions:a)10mol %o fc atalyst III,4equiv of 3, CH 2 Cl 2 ,reflux, 16 h, 19:77%, E > 98 %.…”

Section: Scheme1retrosynthesis Of Etretinate Andcurcumin Analoguesmentioning

confidence: 99%

Synthesis of Aromatic Retinoids and Curcuminoids and Evaluation of their Antiproliferative, Antiradical, and Anti-inflammatory Activities

Morzycki

Rárová²,

Grúz³

et al. 2016

ChemistryOpen

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Natural retinoids and curcuminoids are known for their broad spectrum of biological properties, such as antioxidant, anti‐inflammatory, antitumor, and so forth. In this work, a convenient synthesis of aromatic retinoids and curcuminoids from vinyl or allyl ketones, and the corresponding alcohols, using olefin metathesis as a key reaction, was elaborated. The best yields and diastereoselectivities were obtained from allylic or homoallylic alcohols by employing the two‐step cross‐metathesis/oxidation procedure. The synthesized analogues were tested for their antiproliferative activity on human cancer cell lines of various origin (leukemia CEM, adenocarcinoma MCF7, cervical carcinoma HeLa) as well as for their antioxidant and anti‐inflammatory activity in vitro. All examined derivatives exhibited strong anti‐inflammatory activity in vitro without affecting cell viability. They also showed strong cytotoxicity against leukemia cell line CEM, except for 18 and 35. The antioxidant activity of the tested compounds was rather weak.

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“…In 2002, Saigo and co‐workers first introduced the concept of macrocyclic planar chiral cyclophane‐type imidazolium salts ( 1 a – d ), which was successfully applied as a room temperature ionic liquid with a molecular‐recognition ability . Bimacrocyclic imidazolium salts 1 e – i can be used as precursors for chiral concave NHCs .…”

Section: Introductionmentioning

confidence: 99%

“…In 2002, Saigo and co-workers first introduced the concept of macrocyclic planarc hiral cyclophane-type imidazolium salts (1a-d), whichw as successfully applied as ar oom temperature ionic liquid with am olecular-recognition ability. [11,12] Bimacrocyclic imidazolium salts 1e-i can be used as precursorsf or chiral concaveN HCs. [13] Am acrocyclic fragment on an imidazolium salt can easily be constructed by ring-closing metathesis, whichw as first described by Lüning.…”

Section: Introductionmentioning

confidence: 99%

Well‐Defined Chiral Copper NHC Complex in the Asymmetric Conjugated β‐Borylation and One‐Pot Metathesis‐Asymmetric β‐Borylation Reactions

Jana

Trzybiński

Woźniak

et al. 2017

Chemistry A European J

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Highly stereoselective conjugate β-borylation, using a new chiral NHC-based copper catalyst, has been achieved. The chiral NHC copper complex was prepared in gram scale and showed high enantioselectivity and activity (up to 10 000 turnovers at 100 ppm of catalyst loading). This method was employed in the synthesis of a chiral β-borylated ester from simple unconjugated alkenes though an unprecedented one-pot cross metathesis-asymmetric borylation sequence.

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New olefin metathesis catalysts bearing polyether clamp in N-heterocyclic carbenes ligands

Cited by 14 publications

References 45 publications

New metathesis catalyst bearing chromanyl moieties at the N-heterocyclic carbene ligand

New metathesis catalyst bearing chromanyl moieties at the N-heterocyclic carbene ligand

Synthesis of Aromatic Retinoids and Curcuminoids and Evaluation of their Antiproliferative, Antiradical, and Anti-inflammatory Activities

Well‐Defined Chiral Copper NHC Complex in the Asymmetric Conjugated β‐Borylation and One‐Pot Metathesis‐Asymmetric β‐Borylation Reactions

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