Organocatalytic Enantioselective Synthesis of Polycyclic Benzosultams from 2-Amino-β-nitrostyrenes with Cyclic N-Sulfonyl Ketimines

Organic Letters, Год журнала: 2024, Номер 26(7), С. 1472 - 1477

Опубликована: Фев. 13, 2024

A highly efficient enantioselective [4 + 2] cycloaddition of 2-amino-β-nitrostyrenes with cyclic N-sulfonyl ketimines has been developed. This reaction utilizes an organocatalytic approach, employing a multiple-hydrogen-bonding bifunctional squaramide-based catalyst. The process allows for the precise synthesis chiral polycyclic benzosultams, showcasing intricate structures that incorporate quaternary centers. Noteworthy outcomes this method include high yields excellent enantioselectivities and diastereoselectivities (up to 97% yield, 96% ee, >20:1 dr).

Язык: Английский

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Palladium‐Catalyzed [4+2] and [6+2] Dipolar Cycloadditions for the Construction of Benzo[d]isothiazole 1,1‐Dioxide Fused 1,3‐Oxazinanes and 1,3‐Oxazocanes^†

Chinese Journal of Chemistry, Год журнала: 2023, Номер 42(8), С. 829 - 834

Опубликована: Дек. 8, 2023

Comprehensive Summary The Pd‐catalyzed dipolar cycloaddition represents a significant synthetic strategy for the construction of useful heterocyclic compounds. This study developed [4+2] and [6+2] reactions benzo[ d ]isothiazole 1,1‐dioxides (BDs) leading to synthesis BD‐fused 1,3‐oxazinane 1,3‐oxazocane derivatives, respectively. In particular, 1,3‐oxazinanes demonstrated regio‐ enantioselective characteristics, resulting in products with good yields, enantioselectivity regioselectivity (if applicable). Furthermore, reaction this work represented first medium‐sized ring compounds based on BDs.

Язык: Английский

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Organocatalytic Asymmetric Michael Reactions of Cyclic N-Sulfonylimines with Nitroalkenes or 2-Nitroallylic Acetates

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 25, 2025

A highly efficient enantioselective Michael addition of cyclic N-sulfonylimines with nitroalkenes has been developed, utilizing a bifunctional squaramide catalyst. This approach achieves remarkable results, delivering products high yields and outstanding stereoselectivities, reaching up to 97% yield, >20:1 dr, >99% ee. Furthermore, an asymmetric tandem reaction 2-nitroallylic acetates established. innovative methodology involves Michael/intramolecular aza-Michael cascade, leading the formation enantioenriched benzosultam-fused tricyclic compounds excellent stereoselectivities (up dr ee).

Язык: Английский

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Rhodium-catalyzed addition reactions of benzylic C–H bonds to cyclic N-sulfonyl ketimines via π-coordination

Chinese Chemical Letters, Год журнала: 2023, Номер 35(3), С. 108650 - 108650

Опубликована: Июнь 7, 2023

Язык: Английский

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One-pot π-extension approach of iminoindoles-to-α-carbolines as blue-light emitters using the cooperative basic system

New Journal of Chemistry, Год журнала: 2024, Номер 48(32), С. 14163 - 14169

Опубликована: Янв. 1, 2024

Efficient access to α-carbolines was achieved via a domino reaction between iminoindoles and arylidene malononitriles using DABCO/NaHCO 3 as cooperative basic system. The synthesized scaffolds display blue emissions with good quantum yields.

Язык: Английский

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CeCl₃-Catalyzed C–H Alkylation of N-Sulfonyl Ketimines with Alkanes and Ether via Photoinduced Ligand-to-Metal Charge Transfer

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(24), С. 18337 - 18343

Опубликована: Дек. 9, 2024

A cerium-catalyzed C–H alkylation of N-sulfonyl ketimines with low-cost and readily available alkanes as alkyl sources was developed. This transformation proceeded through the synergy photoinitiated ligand-to-metal charge transfer (LMCT) using a chlorine radical an HAT reagent air green oxidant. series alkylated were synthesized moderate to good yields in highly atom-economic manner under chemical oxidant-free conditions.

Язык: Английский

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Cu(OAc)₂/DABCO-mediated domino reaction of vinyl malononitriles with cyclic sulfamidate imines: access to 6-hydroxyaryl-2-aminonicotinonitriles

Organic & Biomolecular Chemistry, Год журнала: 2021, Номер 20(2), С. 352 - 357

Опубликована: Дек. 11, 2021

An efficient DABCO/Cu(OAc) 2 promoted one-pot access to pharmacologically exciting highly substituted 6-hydroxyaryl-2-aminonicotinonitriles in good high yields is reported.

Язык: Английский

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Regioselective access to di- and trisubstituted pyridines via a metal-oxidant-solvent-free domino reaction involving 3-chloropropiophenones

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(34), С. 6759 - 6765

Опубликована: Янв. 1, 2022

A remarkable metal-oxidant-solvent- and base-free domino route for regioselective access to a wide range of 2,4-di- 2,3,4/6-trisubstituted pyridines including carbo- heterocyclic fused is reported. This [3C + 2C 1N] cyclization reaction occurs between 3-chloropropiophenones (3C units), enolizable acyclic/cyclic ketones (2C sources) NH4OAc as robust N source under neat conditions an open atmosphere, producing new C=C C=N-C bonds in highly chemo- manners. Interestingly, this eco-friendly method has many positive features: excellent functional group tolerance, broad substrate scope, good regioselectivities, promising yields, no-unwanted products, neutral appropriateness large-scale synthesis. Mechanism studies reveal that the situ generated β-amino ketone from 3-chloropropiophenone ammonium salt undergoes C=N bond formation with followed by intramolecular process (C=C bond), which are decisive steps pyridine

Язык: Английский

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AgOTf/Et₃N Cooperative Catalysis Enabled One‐Pot Access to α‐(Indolizinylethyl)‐Substituted N‐Sulfonyl Ketimines via an Imino‐Alkyne Cyclization

Asian Journal of Organic Chemistry, Год журнала: 2022, Номер 11(12)

Опубликована: Ноя. 1, 2022

Abstract The β‐Csp 3 −H functionalization of N‐sulfonyl ketimines with 2‐(2‐enynl)pyridines/quinolines via a cooperative Ag(I)‐/organobase‐catalyzed 5‐ endo‐dig cyclization‐addition reaction is reported. This successive C−N/C−C bond‐making provides simple and atom‐economical technique for granting diverse set 1,3‐disubstituted indolizines/pyrrolo[1,2‐ ]quinolines possessing synthetically resourceful ketimine moiety. Moreover, our designed strategy applies to broad substrates allows various functionalities. Furthermore, this has many imperative synthetic points such as mild conditions, low catalyst loading, acceptable chemical yields highly diastereoselective (up ≤93 : 7 dr). moiety indolizine was easily transmuted into the reputed classes coumarin benzofuran derivatives.

Язык: Английский

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Photoinduced decatungstate-catalyzed direct coupling of cycloalkanes and cyclic aldimines

Green Synthesis and Catalysis, Год журнала: 2023, Номер unknown

Опубликована: Окт. 1, 2023

We first describe a photoinduced decatungstate-catalyzed direct coupling of cycloalkanes and cyclic aldimines. The desired products were generated in moderate to good yields with wide substrate scope under mild reaction conditions. mechanistic study revealed radical process. In addition, the usefulness organic synthesis was proved by scale-up as well late-stage modification drug-like molecules.

Язык: Английский

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