Practical Synthesis of Valbenazine via 1,3‐Dipolar Cycloaddition^†

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 42(8), P. 841 - 845

Published: Dec. 6, 2023

Comprehensive Summary Valbenazine (Ingrezza), a potent and highly selective inhibitor of vesicular monoamine transporter type 2 (VMAT2) through the active metabolite hydrotetrabenazine (HTBZ), has been approved for treatment tardive dyskinesia and, very recently, chorea, which is associated with Huntington's disease. Despite numerous synthetic efforts dedicated to synthesis HTBZ, industrial preparation valbenazine uses dihydroisoquinoline as starting material chiral resolution racemic HTBZ derived from ketone reduction. Herein, we present practical featuring stereoselective 1,3‐dipolar cycloaddition enzymatic kinetic resolution. The cascade process includes cycloaddition, N—O bond cleavage, lactamization, proved be operationally simple. allure developed in this work offers rapid access toward affording tetrahydroisoquinoline (THIQ)‐fused piperidine production medically significant compounds, such yohimbine reserpine.

Language: Английский

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Copper-Catalyzed Sulfinyl Cross-Coupling Reaction of Sulfinamides

Organic Letters, Journal Year: 2022, Volume and Issue: 24(46), P. 8514 - 8519

Published: Nov. 11, 2022

A copper-catalyzed sulfinyl cross-coupling reaction of sulfinamides with aldehyde-derived N-tosylhydrazones is described. This approach enables facile access for the construction structurally diverse sulfoxides via novel and efficient S–N/S–C bond interconversions, features broad substrate scope, accommodates various functional groups as well pharmacophores. Moreover, given could be scaled up to gram scale carried out in a one-pot fashion directly from aldehydes. The utility produced demonstrated by further transformations. preliminary mechanistic investigation was performed, which disclosed possible pathways.

Language: Английский

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Collective syntheses of five abietane-type diterpenoids using a polyene cyclization strategy

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 140, P. 155023 - 155023

Published: March 21, 2024

Language: Английский

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Gold-catalyzed intermolecular tandem cyclization/[4 + 3] cycloaddition of 2-(1-alkynyl)-cyclopropyl pyridines with nitrones: an efficient strategy for the synthesis of [1,2]oxazepino[5,4-a] indolizines

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(13), P. 3685 - 3691

Published: Jan. 1, 2024

A new method for the synthesis of seven-membered heterocycle-fused indolizine scaffolds from 2-(1-alkynyl-cyclopropyl)pyridines and nitrones under catalysis PPh 3 AuNTf 2 .

Language: Английский

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Ytterbium‐Catalyzed Tandem Diels–Alder/Claisen Rearrangement/Decarboxylation of Hetero‐Allenes for the Synthesis of Diarylmethanes

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 43(2), P. 199 - 204

Published: Oct. 17, 2024

Comprehensive Summary A tandem Diels–Alder reaction/Claisen rearrangement/decarboxylation strategy of N ‐allenamides (or aryloxyallenes) with 3‐alkoxycarbonyl‐2‐pyrones has been developed for the efficient synthesis diarylmethanes moderate to good yields. The reaction exhibits functional group tolerance and can be applied late‐stage modifications known drug molecules. Mechanistic studies indicate that ester at 3‐position 2‐pyrones is essential, initial between proximal C=C bond crucial success reaction.

Language: Английский

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Gold-Catalyzed Enantioselective Reactions

Elsevier eBooks, Journal Year: 2023, Volume and Issue: unknown, P. 442 - 465

Published: June 10, 2023

Language: Английский

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Advances in Versatile Chiral Ligands for Asymmetric Gold Catalysis

Catalysts, Journal Year: 2023, Volume and Issue: 13(9), P. 1294 - 1294

Published: Sept. 14, 2023

The formation of valuable chiral skeletons through asymmetric gold catalysis has made considerable progress due to the unrivaled affinity complexes with multiple carbon–carbon bonds. renaissance ligands in recent decades enabled elaborate design complexes, which are great significance control these catalytic reactions. Therefore, this review intends highlight and central role versatile catalysis. Specifically, seminal applications various representative examples gold-catalyzed reactions comprehensively explored. In addition, reaction mechanisms mentioned when crucial interactions between activated substrates introduced. Furthermore, enantioselective construction functional organic materials drug molecules also presented.

Language: Английский

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Recent Progress on [3+2] Ring-Expansion Reaction of Aziridines with Unsaturated Compounds

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(12), P. 4057 - 4057

Published: Jan. 1, 2023

( a 河南师范大学化学化工学院 抗病毒性传染病创新药物全国重点实验室 平原实验室 绿色化学介质与反应教育部

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Enantioselective para‐C(sp²)−H Functionalization of Alkyl Benzene Derivatives via Cooperative Catalysis of Gold/Chiral Brønsted Acid**

Angewandte Chemie, Journal Year: 2022, Volume and Issue: 134(40)

Published: Aug. 4, 2022

Abstract An asymmetric para‐ C(sp 2 )−H bond functionalization of alkyl benzene derivatives was successfully developed via cooperative catalysis gold and chiral phosphoric acid (CPA), leading to synthetically useful 1,1‐diaryl motifs. Chiral acid, ligand, molecular sieves were found be crucial for enantioselectivity control this transformation. The salient features protocol include mild conditions, high efficiency, commercially available starting materials, highly chemo‐ site‐ as well enantioselective aromatic C−H functionalization, broad substrate scope, extensive applications the products. mechanistic studies suggested that two CPAs might involved in induction.

Language: Английский

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Five-membered ring systems with O and N atoms

Progress in heterocyclic chemistry, Journal Year: 2023, Volume and Issue: unknown, P. 351 - 382

Published: Jan. 1, 2023

Language: Английский

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