Decarboxylative [3 + 2] cycloaddition of propargyl cyclic carbonates with C,O-bis(nucleophile)s to access dihydrofuro[3,2-c]coumarins and dihydronaphtho[1,2-b]furans with quaternary center

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(8), С. 1671 - 1675

Опубликована: Янв. 1, 2024

The development of efficient and straightforward strategies for obtaining chiral complex molecules from readily available starting materials is great value in drug discovery. stereodivergent synthesis heterocycles bearing quaternary centers remains a challenge due to inherent steric issues. Herein, we report an enantioselective copper-catalyzed decarboxylative [3 + 2] cycloaddition propargyl cyclic carbonates/carbamates with 4-hydroxycoumarins afford wide range dihydrofuro[3,2-

Язык: Английский

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Phen-2NO, a new C₂-symmetric rigid-featured tetradentate ligand, and its application in the asymmetric alkylation reaction of indoles

New Journal of Chemistry, Год журнала: 2024, Номер 48(15), С. 6670 - 6675

Опубликована: Янв. 1, 2024

A new class of C 2 -symmetric rigid-featured chiral phen ligands that provide the N , O -tetradentate coordination moiety and two additional -dioxides were rationally designed developed.

Язык: Английский

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Naphthyridine–2NO, a new C₂-symmetric rigid tetradentate bimetallic ligand and its application in asymmetric Friedel–Crafts alkylation

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(9), С. 2600 - 2606

Опубликована: Янв. 1, 2024

The development of a series novel and easily accessed chiral naphthyridine-type binucleating ligands for asymmetric catalysis.

Язык: Английский

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Palladium-Catalyzed Decarboxylative Allylic Sulfonylation of Vinyloxazolidine-2,4-diones: Synthesis of γ-Sulfonyl-α,β-unsaturated Amides

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 10, 2025

A palladium-catalyzed decarboxylative allylic sulfonylation reaction of vinyloxazolidine-2,4-diones with inexpensive and readily available sodium sulfinates as reagents has been developed. Under the catalysis Pd(PPh3)4, a wide range γ-sulfonyl-α,β-unsaturated amides can be synthesized in good to excellent yields. The developed protocol is characterized by exclusive regioselectivity, mild conditions, broad substrate scope, functional group tolerance, suitable for gram-scale synthesis.

Язык: Английский

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Squaramide-Catalyzed Aza-Michael/Michael Cyclization Cascade Reaction: One-Pot Enantioselective Construction of Highly Func-tionalized γ-Lactams

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Squaramide-catalyzed asymmetric cyclization of nitroalkenes with 3-benzoylacylamides delivers γ-lactams in 25–90% yield and 71–99% ee broad compatibility.

Язык: Английский

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Cu-Catalyzed Intermolecular Asymmetric Propargylic Substitution of N-Hydroxyphthalimide Esters with Propargyl Carbonates

ACS Catalysis, Год журнала: 2023, Номер 13(20), С. 13735 - 13742

Опубликована: Окт. 11, 2023

Transition-metal-catalyzed asymmetric allylic alkylation is one of the most powerful and well-known strategies for construction C–C bonds; nevertheless, propargylation elusive remains far less explored. Here, we report copper-catalyzed propargylic substitution N-acyl phenylglycine N-hydroxyphthalimide (NHP) esters racemic carbonates, which afforded multifunctionalized products bearing a terminal alkyne unit in high yields with good stereoselectivities. Moreover, product can be readily derivatized into other interesting compounds that have great potential exploitation pharmaceutically relevant molecules.

Язык: Английский

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Design and Synthesis of Rigid‐Featured Tertiary Amine‐Derived C₂‐Symmetric Chiral Furan‐N,N′‐dioxide Ligands

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(42)

Опубликована: Авг. 19, 2023

Abstract To expand the chemical space of chiral N ‐oxides and furan‐containing ligands, herein we designed synthesized a new class rigid‐featured tertiary amine‐derived C 2 ‐symmetric furan‐ , N′ ‐dioxide (Fu‐2NO) ligands from optically pure l ‐prolinamides/hydroxylprolinamides in operationally simple two steps up to 57 % overall yield. The newly developed Fu‐2NO possesses pyrroloimidazolone‐based as non‐flat walls, afforded opportunity for fine‐tuning ligand electronic conformational properties by judicious choice substituent nonligating nitrogen atom. More importantly, can tolerate air moisture such that no special handling is needed their storage, be applied Ni(II)‐catalyzed asymmetric Friedel‐Crafts alkylation reaction indole.

Язык: Английский

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Regioselectivity Switch of α-Amino Acid-Derived Esters and MBH Carbonates for the Synthesis of Allyl-Substituted Azlactones

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(6), С. 3800 - 3808

Опубликована: Фев. 28, 2024

Allylic azlactones are greatly significant in terms of potential bioactivities and synthetic applications. Owing to the burgeoning interest pharmaceutical industry α

Язык: Английский

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Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition

Chinese Chemical Letters, Год журнала: 2024, Номер 35(12), С. 109688 - 109688

Опубликована: Март 1, 2024

Язык: Английский

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A palladium-catalyzed decarboxylative (5 + 5) cyclization reaction of vinyloxazolidine-2,4-diones: access to ten-membered N,O-containing heterocycles

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(15), С. 4131 - 4137

Опубликована: Янв. 1, 2024

A palladium-catalyzed decarboxylative (5 + 5) cyclization reaction of vinyloxazolidine-2,4-diones for the synthesis ten-membered N,O-containing heterocycles is disclosed.

Язык: Английский

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