Regioselective and asymmetric allylic alkylation of vinyl epoxides for the construction of allylic alcohols via synergistic catalysis

Science China Chemistry, Год журнала: 2023, Номер 67(2), С. 542 - 550

Опубликована: Ноя. 17, 2023

Язык: Английский

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Catalytic enantioselective synthesis of chiral sulfonium ylides with S-stereogenic center

Chem, Год журнала: 2023, Номер 9(6), С. 1495 - 1504

Опубликована: Март 21, 2023

Язык: Английский

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Sequence [2,3]‐Sigmatropic Rearrangement: One‐Pot Synthesis of Propargyl Allenylamines

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(18), С. 2223 - 2227

Опубликована: Май 14, 2024

Comprehensive Summary Allenes, served as highly sought‐after building blocks, are an indispensable component of synthetic chemistry. Their utility in modulating the chemical, physical, and pharmaceutical properties organic compounds make allenes a desirable choice various applications. Here, we report facile method for atom‐economical synthesis propargyl allenylamines via underdeveloped [2,3]‐sigmatropic rearrangement. Our strategy employs easily accessible propargylamines starting materials, which first converted into ammonium salts, followed by base‐promoted This one‐pot, two‐step reaction proceeds absence transition metals, displays very broad scope, does not require introduction electron‐withdrawing group materials.

Язык: Английский

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Tandem catalytic allylic C–H amination and asymmetric [2,3]-rearrangement via bimetallic relay catalysis

Chemical Science, Год журнала: 2024, Номер 15(33), С. 13299 - 13305

Опубликована: Янв. 1, 2024

An asymmetric tandem allylic C–H amination and [2,3]-sigmatropic rearrangement has been developed by making use of bimetallic relay catalysis with an achiral Pd(0) catalyst a chiral N,N ′-dioxide-Mg( ii ) complex.

Язык: Английский

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Stereoselective Synthesis of Atropisomeric Amides Enabled by Intramolecular Acyl Transfer

Chemical Science, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

A stereoselective strategy to make C–N atropisomeric amides based on intramolecular acyl transfer via a tethered Lewis basic pyridine or tertiary amine group is reported.

Язык: Английский

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Recent Advances in the Synthesis of Amino Acid Derivatives through Multicomponent Reactions

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

Опубликована: Март 11, 2025

Abstract Amino acids play significant roles in the study of life sciences, pharmaceutical R&D, bioengineering, and so on. Artificial amino acid‐based drugs are important advancing therapeutic innovation for multiple diseases including chronic pain, diabetes, Alzheimer's disease. On other hand, multicomponent reactions (MCRs) demonstrated to be a powerful strategy construction complicated structures from readily accessible starting reagents one pot. Thus, applying preparation their derivatives can potent research chemistry. With rapid development various catalytic methods reactions, this review outlines recent acid by transition metal‐catalyzed, light‐mediated organocatalytic reactions.

Язык: Английский

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Divergent Construction of α,α-Difunctionalized Ketones via [1,2]-Sigmatropic Rearrangement/Alkylation-Hydroxylation/Dialkylation of I^(III)/S^(VI) Ylides

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 1, 2025

The rare [1,2]-sigmatropic rearrangement of sulfoxonium-iodonium hybrid ylides is described, which enables the efficient sulfoxidation/sulfonylation-alkylation I(III)/S(VI) with 1,3-dicarbonyls. By slight modification reaction conditions, controllable alkylation-hydroxylation and dialkylation were achieved. This strategy affords a diverse array α,α-difunctionalized ketones in moderate to good yields, demonstrating broad substrate scope. These findings provide an important advancement sulfoxonium highlight divergent reactivity ylides.

Язык: Английский

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Silver-Catalyzed Doyle–Kirmse Reaction of Allyl Sulfides with Vinyl Triftosylhydrazones

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 7, 2025

Here, we report a general and practical Doyle-Kirmse reaction of allyl/propargyl sulfides with donor-only vinyl carbenes generated in situ from triftosylhydrazones the presence silver catalyst. This protocol features mild conditions, exhibits broad substrate scope exceptional functional group tolerance, provides corresponding 1,5-dienyl 1,4-enallenyl high yields. Moreover, gram-scale synthesis, late-stage modifications complex molecules, post-synthetic transformations were performed to demonstrate applicability this protocol.

Язык: Английский

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N-Polyfluoroarylation-Triggered Rearrangement of Enesulfinamidines: Asymmetric Synthesis of α-Amino Ketimine Derivatives

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

Опубликована: Май 21, 2025

Metalloenamines, generated through the α-deprotonation of N-iminosulfinyl ketimines, can be selectively intercepted at their nitrogen atom by highly fluorinated (hetero)arenes. The interaction leads to formation N-polyfluoroarylated enesulfinamidine intermediates, which are capable undergoing [2,3]-sigmatropic rearrangement yield α-amino ketimine derivatives. high enantiopurity resulting products is ensured precise transfer chirality from sulfur iminosulfinyl group α-carbon moiety.

Язык: Английский

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Cobalt(II)-Catalyzed Enantioselective Propargyl Claisen Rearrangement: Access to Allenyl-Substituted Quaternary β-Ketoesters

Organic Letters, Год журнала: 2023, Номер 25(39), С. 7105 - 7109

Опубликована: Сен. 21, 2023

Highly enantioselective propargyl Claisen rearrangement of O-propargyl β-ketoesters was achieved under 2.5 mol % the chiral cobalt complex as catalyst mild reaction conditions. With Co(OTf)2 Lewis acid and C1-symmetric imidazoline-pyrroloimidazolone pyridine ligand, diverse allenyl-substituted all-carbon quaternary were obtained in good yields (up to 97% yield) high enantioselectivities 98% ee).

Язык: Английский

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