A concise deracemization of racemic secondary and tertiary amines with a tetrahydroisoquinoline core has been successfully realized by orchestrating redox process consisted N-bromosuccinimide oxidation iridum-catalyzed asymmetric hydrogenation. This compatible combination enables one-pot, single-operation to generate chiral 1-substituted 1,2,3,4-tetrahydroisoquinolines up 98% ee in 93% yield, offering simple scalable synthetic technique for directly from starting materials.

The photoexcited state lifetimes of iron complexes are typically much shorter than those iridium and ruthenium complexes. For that reason, find less application in photochemical organic synthesis. Through photocatalysis, a mild effective protocol for decarboxylative C–C C–N bond formation has been achieved. carboxylic acids readily undergo radical decarboxylation the presence Fe 2 (SO 4 ) 3 di‐(2‐picolyl)amine under visible light irradiation. resulting alkyl radicals then react with Michael...

Arylboronsäuren können unter Nickelkatalyse monofluoriert werden. Die Nützlichkeit dieser Methode wird beispielhaft anhand der Monofluormethylierung borylierter und Acyl-geschützter Derivate des Statinwirkstoffs Ezetimib gezeigt. Mechanistische Studien deuten darauf hin, dass ein Fluormethylradikal am NiI/NiIII-Katalysezyklus beteiligt ist. As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed may be...

A chiral phosphoric acid catalyzed asymmetric transfer hydrogenation of aromatic amines, quinolin-3-amines, was successfully developed with up to 99% ee. To supplement our previous work on the Ir-catalyzed 2-alkyl substituted a number 2-aryl substrates were reduced provide series valuable exocyclic amines high diastereo- and enantioselectivities.

A facile access to optically active cyclic ureas was developed through palladium-catalyzed asymmetric hydrogenation of pyrimidines containing tautomeric hydroxy group with up 99 % ee. Mechanistic studies indicated that reaction pathway proceed C=N the oxo tautomer pyrimidin-2(1H)-one, acid-catalyzed isomerization enamine-imine, and imine pathway. In addition, chiral are readily converted into useful 1,3-diamine thiourea derivatives without loss optical purity.

A facile method has been developed for the synthesis of chiral piperazines through Ir-catalyzed hydrogenation pyrazines activated by alkyl halides, giving a wide range including 3-substituted as well 2,3- and 3,5-disubstituted ones with up to 96% ee. The high enantioselectivity, easy scalability, concise drug demonstrate practical utility.

Rapid and efficient access to structurally diverse β-fluoroalkylamines is in high demand, with their wide presence great importance medicinal chemistry drug development. Direct 1,2-aminofluorination of alkenes offers an ideal strategy for one-step entry β-fluorinated amines from readily available starting materials. Yet the synthesis valuable alkylamines remains unsolved challenge, due inherent incompatibility between electrophilic fluoride sources electron-rich alkylamines. We report...

An efficient iridium-catalyzed hydrogenation of 4,6-disubstituted 2-hydroxypyrimidines has been achieved, giving chiral cyclic ureas with excellent diastereoselectivities and up to 96% ee enantioselectivities. In the presence in situ generated hydrogen halide, equilibrium lactame–lactime tautomerism 2-hydroxypyrimidine is more toward oxo form lower aromaticity, which effectively improves reactivity facilitate hydrogenation. Moreover, could be readily converted into 1,3-diamine derivatives...

An iridium-catalyzed asymmetric hydrogenation of cyclic iminium salts has been developed, affording products with up to 96% ee.

Chiral phosphoric acid-catalyzed transfer hydrogenation of 2-hydroxypyrimidines has been successfully realized using Hantzsch ester or dihydrophenanthridine as the hydrogen source, furnishing chiral 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) with excellent yields and enantioselectivities ≤99%. Notably, a novel kind DHPMs an alkyl stereogenic center can be prepared through highly chemoselective hydrogenation.

Herein, we reported iridium-catalyzed asymmetric hydrogenation of quinazolinones with up to 98% ee and excellent yields.

A palladium-catalyzed asymmetric hydrogenation of pyrazines containing a tautomeric hydroxyl group was developed, providing facile access to chiral disubstituted piperazin-2-ones with excellent diastereoselectivities and enantioselectivities.

An efficient one-pot redox deracemization of the phosphonic ester substituted 3,4-dihydropyrimidin-2-one (DHPM) derivatives is described, providing a series optically active phosphonate DHPMs with up to 96% ee.

Abstract A facile access to optically active cyclic ureas was developed through palladium‐catalyzed asymmetric hydrogenation of pyrimidines containing tautomeric hydroxy group with up 99 % ee . Mechanistic studies indicated that reaction pathway proceed C=N the oxo tautomer pyrimidin‐2(1 H )‐one, acid‐catalyzed isomerization enamine–imine, and imine pathway. In addition, chiral are readily converted into useful 1,3‐diamine thiourea derivatives without loss optical purity.

Aryl boronic acids can be monofluoromethylated under nickel catalysis. The utility of this method is demonstrated by the monofluoromethylation a borylated and acyl-protected derivative statin drug ezetimibe. Mechanistic investigations indicate that fluoromethyl radical involved in NiI/NiIII catalytic cycle. incorporation fluorine atoms into small organic molecules often drastically enhance metabolic stability, lipophilicity, bioavailability, also increase receptor-binding affinity...

Abstract A highly stereocontrolled asymmetric transfer hydrogenation of quinolin‐3‐amines is developed using Hantzsch ester in the presence BINOL‐derived phosphoric acid catalysts.

Abstract Thorough adjustment of the hydrogen pressure and ligands allows for preparation 3‐substituted, 3,5‐ as well 2,3‐disubstituted pyrazines from corresponding pyrazine salts.

Abstract The reaction of phenylsulfonyl or ester activated monofluoro monohalomethanes with arylboronic acids is achieved in the presence a nickel catalyst to yield corresponding fluoromethylaryl derivatives.