Enantioselective Friedel Crafts Reaction Research Articles

ChemInform Abstract: Highly Enantioselective Friedel—Crafts Reaction of Indole with Alkylidenemalonates Catalyzed by Heteroarylidene Malonate‐Derived Bis(oxazoline) Copper(II) Complexes.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Facile Creation of 3‐Indolyl‐3‐hydroxy‐2‐oxindoles by an Organocatalytic Enantioselective Friedel–Crafts Reaction of Indoles with Isatins

AbstractThe first direct enantioselective Friedel–Crafts reaction of indoles with isatins has been developed. The process is catalyzed by simple cupreine under mild reaction conditions and affords synthetically and biologically interesting, chiral 3‐indolyl‐3‐hydroxy‐2‐oxindoles in good yields (68–97%) and with high enantioselectivities (76–91%).

ChemInform Abstract: Highly Enantioselective Friedel—Crafts Reaction of Thiophenes with Glyoxylates: Formal Synthesis of Duloxetine.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Squaramide-catalyzed enantioselective Friedel-Crafts reaction of indoles with imines.

Chiral squaramides are highly enantioselective catalysts for Friedel-Crafts reaction of indoles with N-tosyl imines, affording 3-indolyl methanamine products in 85-96% yields and 84-96% ees.

Highly Enantioselective Friedel–Crafts Reaction of Indole with Alkylidenemalonates Catalyzed by Heteroarylidene Malonate‐Derived Bis(oxazoline) Copper(II) Complexes

AbstractA series of cheap and easily accessible heteroarylidenemalonate‐derived bis(oxazoline) ligands 1 and 2 were synthesized and their copper(II) complexes were applied to the catalytic Friedel–Crafts reaction between indoles and diethyl alkylidenemalonates, Excellent asymmetric enantioselectivities were afforded for the S‐enantiomer (up to >99% ee) in isobutyl alcohol, and the R‐enantiomer (up to 96.5% ee) in dichloromethane.

ChemInform Abstract: Enantioselective Friedel—Crafts Reactions of Ethenetricarboxylates and Substituted Pyrroles and Furans and Intramolecular Reaction of Benzene Derivatives.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Enantioselective Friedel—Crafts Reactions in Water Using a DNA‐Based Catalyst.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Friedel-Crafts Alkylation of Indoles with a Cu-DNA Catalyst

An impressive example of an enantioselective Friedel-Crafts reaction using water and a DNA-based catalyst is described. The catalyst is assembled in situ from Cu-dmbpy and salmon testes DNA, which is readily available and inexpensive. The reaction is compatible with a ­variety of substituents on the indole and olefin, ­although in some cases, using other DNA strands provided more optimal results. Results for both analytical and preparative scales are reported.

Enantioselective Friedel–Crafts reactions of ethenetricarboxylates and substituted pyrroles and furans and intramolecular reaction of benzene derivatives

Compared to enantioselective Friedel–Crafts reactions of indoles, reactions of alkylidene malonates with monocyclic aromatic compounds generally proceed with low enantioselectivity. The Friedel–Crafts reactions of ethenetricarboxylates 1 and monocyclic heteroaromatic compounds, such as substituted pyrroles and furans were investigated. The reaction of 1 with 2,4-dimethylpyrrole in the presence of a chiral bisoxazoline–copper(II) complex (10 mol %) in tetrahydrofuran at room temperature gave alkylated products in up to 72% ee. The reaction of 1 with 2-substituted furans gave alkylated products in 46–62% ee. The absolute stereochemistry of the furan Friedel–Crafts product 7e was determined by transformation to the known 2,3-dimethylbutyric acid. The intramolecular reaction of benzene derivatives gave cyclized products up to 56% ee.

Efficient Friedel-Crafts Alkylation of 4,7-Dihydroindoles with Nitroolefins

In this paper a highly efficient enantioselective Friedel-Crafts reaction of 4,7-dihydro-indoles with nitroolefins catalyzed by the chiral phosphoric acid (S)-PA was reported. By slowly adding nitroolefins with a syringe pump, the Friedel-Crafts alkylation of 4,7-dihydroindoles with nitroolefins proceeded effectively with 0.5 mol% of (S)-PA, providing the corresponding alkylation products in high yields (93-98%) and excellent enantioselectivities (er up to 98.5:1.5). After a subsequent oxidation step with 4-benzoquinone, the alkylation products can be converted into 2-substituted indoles, which can be further transformed to enantioenriched tetrahydro-γ-carbolines without erosion of enantiomeric ­excesses.

Enantioselective Friedel–Crafts Reactions in Water Using a DNA‐Based Catalyst

AbstractIns kühle Nass: Bei der ersten Lewis‐Säure‐katalysierten asymmetrischen Friedel‐Crafts‐Alkylierung mit Olefinen in Wasser genügen schon 0.15 Mol‐% eines DNA‐Kupfer‐Katalysators, um in der Reaktion von α,β‐ungesättigten 2‐Acylimidazolen mit heteroaromatischen π‐Nucleophilen gute Ausbeuten und Enantioselektivitäten zu erzielen (siehe Schema; dmbpy=4,4′‐Dimethyl‐2,2′‐bipyridin).magnified image

Enantioselective Friedel–Crafts Reactions in Water Using a DNA‐Based Catalyst

Taking the plunge: The first example of a Lewis acid catalyzed asymmetric Friedel-Crafts alkylation with olefins in water is described. By using loadings of a DNA-based copper catalyst as low as 0.15 mol %, good yields and excellent enantioselectivities were obtained in the reaction of alpha,beta-unsaturated 2-acyl imidazoles with heteroaromatic pi nucleophiles. dmbpy = 4,4'-dimethyl-2,2'-bipyridine.

ChemInform Abstract: Highly Enantioselective Friedel—Crafts Reaction of 4,7‐Dihydroindoles with β,γ‐Unsaturated α‐Keto Esters by Chiral Broensted Acids.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Highly Enantioselective Friedel—Crafts Reaction of Indoles with 2‐EnoylPyridine 1‐Oxides Catalyzed by Chiral Pyridine 2,6‐Bis(5′,5′‐diphenyloxazoline)—Cu(II) Complexes.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Enantioselective synthesis of (3-indolyl)glycine derivatives via asymmetric Friedel–Crafts reaction between indoles and glyoxylate imines

Chiral phosphoric acid-catalyzed enantioselective Friedel–Crafts reaction of indoles with ethyl glyoxylate imines was developed. With 10 mol % of the catalyst, the Friedel–Crafts reactions between a wide range of indoles and imines have been carried out, affording optically active (3-indolyl)glycine derivatives with excellent yields and high enantioselectivities (up to 87% ee).

Highly Enantioselective Friedel–Crafts Reaction of 4,7‐Dihydroindoles with β,γ‐Unsaturated α‐Keto Esters by Chiral Brønsted Acids

AbstractA highly efficient Friedel–Crafts reaction of 4,7‐dihydroindoles with β,γ‐unsaturated α‐keto esters by a chiral N‐triflyl phosphoramide was realized, affording the 2‐substituted 4,7‐dihydroindoles with up to 98% ee for a wide range of substrates. The Friedel–Crafts alkylation together with a subsequent oxidation of the product with p‐benzoquinone led to a 2‐alkylated indole derivative in 98% ee.

Cu(OTf) 2/trisoxazoline catalyzed asymmetric Friedel–Crafts reaction of pyrroles with alkylidene malonates

In the presence of catalytic amount of Cu(OTf) 2/trisoxazoline, an enantioselective Friedel–Crafts reaction of N-methyl pyrrole with alkylidene malonates has been developed and up to 66% ee is achieved.

Highly Enantioselective Friedel−Crafts Reaction of Indoles with 2-EnoylPyridine 1-Oxides Catalyzed by Chiral Pyridine 2,6-Bis(5′,5′-diphenyloxazoline)−Cu(II) Complexes

The catalytic enantioselective Friedel-Crafts reaction of indoles with 2-enoylpyridine 1-oxides has been studied in the presence of chiral pyridine 2,6-bis(5',5'-diphenyloxazoline)-Cu(II) complexes. The reaction furnished alkylated indoles in excellent yields (up to 97%) and enantioselectivities (up to 99% ee).

ChemInform Abstract: Highly Enantioselective Friedel—Crafts Reaction of 4,7‐Dihydroindoles with Imines by Chiral Phosphoric Acids: Facile Access to 2‐Indolyl Methanamine Derivatives.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Highly Enantioselective Friedel–Crafts Reaction of 4,7‐Dihydroindoles with Imines by Chiral Phosphoric Acids: Facile Access to 2‐Indolyl Methanamine Derivatives

Highly Enantioselective Friedel–Crafts Reaction of 4,7‐Dihydroindoles with Imines by Chiral Phosphoric Acids: Facile Access to 2‐Indolyl Methanamine Derivatives