Stand and deliver: The first highly regio- enantioselective bromoamination of chalcones has been developed which proceeds via an unusual bromonium-based mechanism to deliver the title compounds. Excellent results were obtained using 0.05 mol % C2-symmetric N,N′-dioxide/scandium(III) complex under mild conditions (see scheme). Detailed facts importance specialist readers are published as ”Supporting Information”. Such documents peer-reviewed, but not copy-edited or typeset. They made...

Abstract An efficient nickel‐catalyzed decarbonylative amination reaction of aryl and heteroaryl esters has been achieved for the first time. The new protocol allows direct interconversion amides into corresponding amines represents a good alternative to classical rearrangements as well cross coupling reactions.

Highly efficient catalytic chloroamination reaction of α,β-unsaturated γ-keto esters and chalcones has been developed via a chloronium-based mechanism to deliver anti-regioselective vicinal chloroamines instead the aziridinium intermediates delivered aminochlorides. The combination TsNCl(2) TsNH(2) as reagents made transformation highly efficient, delivering γ-carbonyl-β-chloro-α-amino acid derivatives α-chloro-β-amino-ketone in nearly quantitative yields with up 99% ee 99:1 dr under...

A protocol for the photooxidative activation of α-silylamines and α-amino acids desilylative decarboxylative additions, allylations, heteroarylations in presence graphitic carbon nitride (g-C3N4) was developed. The procedure has broad scope provides desired products high yields. heterogeneous nature g-C3N4 catalytic system enables easy recovery recycling as well use multiple runs without loss activity. photoredox catalyzed reactions can also be conducted continuous photo flow fashion scaled...

Asymmetric expansion: A catalytic asymmetric ring-expansion reaction of the title compounds occurs in presence a Sc(OTf)(3) catalyst bearing an N,N'-dioxide-based ligand. Highly functionalized 2-quinolone derivatives containing chiral C4-quaternary stereocenter were obtained high yields and levels selectivity under mild conditions (see scheme; Tf=trifluoromethanesulfonyl).

A visible light mediated metal-free heterogeneous photocatalytic system has been developed for highly efficient benzylic C–H oxygenations utilizing graphitic carbon nitride (g-C₃N₄) as a recyclable, nontoxic and low cost photocatalyst.

Abstract The development of heterogeneous metallaphotocatalysis is great interest for sustainable organic synthesis. rational design and controllable preparation well-defined (site-isolated) metal/photo bifunctional solid catalysts to meet such goal remains a critical challenge. Herein, we demonstrate the incorporation privileged homogeneous bipyridyl-based Ni-catalysts into highly ordered crystalline potassium poly(heptazine imide) (K-PHI). A variety PHI-supported cationic (L n Ni-PHI) have...

An enantioselective one-pot synthesis of 2-amino-4-(indol-3-yl)-4H-chromenes via a Knoevenagel/Pinner/Friedel–Crafts reaction salicylaldehyde, malononitrile, and indole is presented. Moderate to good yields (up 89%) high enantioselectivities 90% ee) were obtained with an N,N′-dioxide–Zn(II) complex as the catalyst. This strategy provides efficient convenient method access enantiomerically enriched 2-amino-4H-chromene derivatives.

Abstract Asymmetric catalysis : A facile enantioselective Strecker reaction of ketimines with trimethylsilyl cyanide (TMSCN) was realized by employing chiral ( S )‐BNPNa 3 e and PBAP as an additive (see image). wide substrate scope good‐to‐excellent enantioselectivities were achieved. magnified image efficient catalyzed a alkali‐metal salt has been developed. When 10 mol % BNPNa (BNP=1,1′‐binaphthyl‐2,2′‐diylphosphate) prepared in situ para ‐ tert ‐butyl‐ ortho ‐adamantylphenol (PBAP)...

Catalytic asymmetric sulfenylation of unprotected 3-substituted oxindoles has been developed via cooperative catalysis a chiral N,N′-dioxide–Sc(OTf)3 complex and Brønsted base. Utilizing readily available N-(phenylthio)phthalimide as the sulfur source, wide range optically active 3-phenylthiooxindoles were obtained in excellent yields with enantioselectivities under mild reaction conditions.

Ramping it up: The titled reaction has been developed using a chiral N,N′-dioxide–LaIII complex as the catalyst. proceeded with high yield and enantioselectivity. Remarkably, asymmetric amplification was observed, 98 % ee achieved 1 mol L/La(OTf)3 in which value of L 2 ee. Tf=trifluoromethanesulfonyl. Detailed facts importance to specialist readers are published "Supporting Information". Such documents peer-reviewed, but not copy-edited or typeset. They made available submitted by authors....

Add a ring: A catalytic asymmetric [8+2] cycloaddition reaction of azaheptafulvenes with alkylidene malonates was developed. When employing amounts chiral N,N′-dioxide L–NiII complex, the afforded functionalized cycloheptatriene-fused pyrrole derivatives in excellent yields (up to 99 %), diastereoselectivities (>95:5 d.r.), and enantioselectivities (91–97 % ee) under mild conditions. As service our authors readers, this journal provides supporting information supplied by authors. Such...

Highly diastereo- and enantioselective iodoamination of chalcones, 4-aryl-4-oxobutenoates, a trifluoro-substituted enone has been accomplished in the presence chiral N,N'-dioxide/[Sc(OTf)(3)] complex (0.5-2 mol%), delivering desired vicinal anti-α-iodo-β-amino carbonyl compounds regioselectively high yields (up to 97%) with excellent diastereoselectivities (>99:1 d.r.) enantioselectivities 99% ee). Enantiopure syn-α-iodo-β-amino products could also be obtained from isomerization particular...

The catalytic enantioselective fluorination of N-H-free 3-substituted oxindoles was accomplished by a Sc(III)/N,N'-dioxide complex. Under mild reaction conditions, series 3-aryl- and 3-alkyl-3-fluoro-2-oxindoles were obtained in excellent yields (up to 98%) enantioselectivities 99% ee) using N-fluorobisbenzenesulfonimide (NFSI) as the agent. MaxiPost synthesized efficiently 81% yield with 96% ee.

The first iron(III)/N,N'-dioxide-catalyzed asymmetric haloamination of 3-alkylidene- and 3-arylidene-indolin-2-ones was developed, affording the corresponding chiral oxindole derivatives bearing vicinal haloamine substituents with excellent results (up to 99% yield, ee, >19 : 1 dr). This iron catalyst also exhibits perfect enantioselectivity for chalcone derivatives. cooperative activation substrate reagent in concert guarantees high stereoselectivity.

Abstract The first catalytic asymmetric Piancatelli reaction is reported. Catalyzed by a chiral Brønsted acid, the rearrangement of wide range furylcarbinols with series aniline derivatives provides valuable aminocyclopentenones in high yields as well excellent enantioselectivities and diastereoselectivities. value aza‐Piancatelli was demonstrated synthesis cyclopentane‐based hNK1 antagonist analogue.

Heterogeneous photocatalysis has emerged as a green and sustainable technique in organic synthesis. Developing highly effective heterogeneous photocatalysts that outperformed classical ruthenium-/iridium-based homogeneous ones for the visible-light mediated transformations is actively pursued by chemists but remains challenging. Herein, modified carbon nitride-based photocatalytic system both decarboxylative addition reductive dimerization of para-quinone methides been developed. The...

A Cu-doped carbon nitride-based heterogeneous metallaphotocatalytic α-alkynylation of tertiary amines has been developed, allowing for green and sustainable synthesis diverse valuable propargylamines with high efficiency.

A simple and highly efficient N,N'-dioxide organocatalyst system was developed for the asymmetric alpha-chlorination of cyclic beta-ketoesters using easily available NCS as chlorine source to provide a series optically active alpha-chloro-beta-ketoesters in excellent yields with 90-98% ee.

A catalytic asymmetric intra- and intermolecular haloetherification of electron-deficient alkenes (halogen = Cl, Br, I) has been realized by the use chiral metal complexes N,N′-dioxides. In presence a Fe(III) complex, series tetrahydropyran derivatives were obtained in good yields (up to 99% yield) with high level enantioselectivities 97% ee). Promoted Ce(III) oxepane could be given results. Moreover, chalcones catalyzed Sc(III) complex using MeOH as nucleophile is demonstrated. This...

Abstract A highly efficient chiral N,N′ ‐dioxide–nickel(II) complex system has been developed to catalyze the domino thia‐Michael/aldol reaction of 1,4‐dithiane‐2,5‐diol with 3‐alkenyloxindoles. series desired spirocyclic oxindole‐fused tetrahydrothiophenes was obtained in good yields excellent ee and dr (up 97% yield, 98% , >19:1 ). Besides, based on X‐ray crystal structure catalyst as well absolute configuration product, a catalytic model proposed explain stereocontrol process. magnified image

Halofunctionalization methods enable the vicinal difunctionalization of alkenes with heteroatom nucleophiles and halogen moieties. As a fundamental transformation in organic synthesis, catalytic asymmetric variants have only recently been reported. In sharp contrast to halocyclization simple which involves nucleophile-assisted alkene activation process, halofunctionalization enones developed by our laboratory features an electrophile-assisted 1,4-addition pathway. Our work this area has...

Sparsam mit dem Katalysator: In der unter milden Bedingungen über eine Bromonium-Zwischenstufe verlaufenden Titelreaktion wurden 0.05 Mol-% eines C2-symmetrischen N,N′-Dioxid-Scandium(III)-Komplexes hervorragende Resultate erzielt (siehe Schema). Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents peer-reviewed, but not copy-edited or typeset. They made available submitted by the authors. Please note: The publisher is responsible for...

Asymmetrische Expansion: Ein Sc(OTf)3-Katalysator mit einem N,N′-Dioxid-basierten Liganden bewirkt die katalytische asymmetrische Ringerweiterung der Titelverbindungen. Dabei werden unter milden Reaktionsbedingungen hoch funktionalisierte 2-Chinolone chiralen quartären C4-Stereozentrum in hoher Ausbeute und Selektivität erhalten (siehe Schema; Tf=Trifluormethansulfonyl). Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents...