4.8 Article

Skeleton-Reorganizing Coupling Reactions of Cycloheptatriene and Cycloalkenones with Amines

相关参考文献

注意:仅列出部分参考文献,下载原文获取全部文献信息。
Article Chemistry, Multidisciplinary

Bioinspired and Ligand-Regulated Unnatural Prenylation and Geranylation of Oxindoles with Isoprene under Pd Catalysis

Chao-Yang Zhao et al.

Summary: In this study, bioinspired unnatural prenylation and geranylation of oxindoles using isoprene as the feedstock under Pd catalysis and ligand regulation were demonstrated. Pentenylated and geranylated oxindoles were obtained with high selectivity by switching ligands. Additionally, the head-to-head product could be further transformed to an internal skipped diene under Pd-H catalysis. No stoichiometric by-product was generated in the process.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Multidisciplinary Sciences

Scaffold hopping by net photochemical carbon deletion of azaarenes

Jisoo Woo et al.

Summary: Discovery chemists use an iterative structural optimization method to identify purpose-tailored molecules, but the preparation of each candidate rarely matches their thought process. We report a method that allows chemists to directly switch between chemically distinct heteroaromatic scaffolds, addressing part of this problem.

SCIENCE (2022)

Article Chemistry, Multidisciplinary

Palladium-catalysed construction of butafulvenes

Xin Huang et al.

Summary: This article reports an efficient palladium-catalyzed coupling protocol for the rapid assembly of symmetric butafulvene derivatives. Two complementary mechanisms involving palladium catalysis were confirmed through mechanistic studies, enabling the synthesis of non-symmetric butafulvenes. The advantages of this strategy include mild reaction conditions, simple catalytic systems, and easy scalability. The synthetic potential of the products as platform molecules for cyclobutene derivatives was also demonstrated.

NATURE CHEMISTRY (2022)

Article Chemistry, Physical

Nickel-catalysed asymmetric heteroarylative cyclotelomerization of isoprene

Gong Zhang et al.

Summary: The atom-economic reaction of heteroarylative telomerization of isoprene with heterocycles provides an efficient enantioselective transformation method for creating an unnatural monoterpene framework, which may exhibit different biological activities.

NATURE CATALYSIS (2022)

Article Chemistry, Physical

CPA-catalyzed multicomponent reaction of anilines, aldehydes, and azetidinones: Rapid access to enantiopure-fused azetidines

Lei-Lei Qian et al.

Summary: This study introduces a chiral phosphoric acid-catalyzed multicomponent reaction method for the efficient synthesis of fused azetidines with specific stereochemistry, with high yields and broad functional group tolerance.

CHEM CATALYSIS (2022)

Article Chemistry, Multidisciplinary

Fe-Catalyzed Anaerobic Mukaiyama-Type Hydration of Alkenes using Nitroarenes

Anup Bhunia et al.

Summary: This study reports a highly diastereoselective Fe-catalyzed anaerobic Markovnikov-selective hydration of alkenes using nitroarenes as oxygenation reagents. The method features excellent Markovnikov-selectivity, large functional group tolerance, and applicability for late-stage chemical functionalization. The anaerobic protocol outperforms existing hydration methodology in terms of reaction efficiency and selectivity.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Photocatalytic Aerobic Oxidative Ring Expansion of Cyclic Ketones to Macrolactones by Cerium and Cyanoanthracene Catalysis

Jianbo Du et al.

Summary: A cerium-catalyzed aerobic oxidative ring expansion method using cyanoanthracene as a co-catalyst has been developed for the rapid construction of challenging macrolactones under visible light conditions, demonstrating the potential to simplify the generation of molecular complexity and enabling the concise synthesis of sonnerlactone.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Orthogonal Regulation of Nucleophilic and Electrophilic Sites in Pd-Catalyzed Regiodivergent Couplings between Indazoles and Isoprene

Wen-Shuang Jiang et al.

Summary: This study demonstrates an orthogonal regulation of nucleophilic and electrophilic sites in the regiodivergent hydroamination of isoprene with indazoles. By choosing appropriate ligands for electrophilic sites on isoprene and acid co-catalysts for nucleophilic sites on indazoles, different insertion pathways can be controlled. Preliminary experimental studies have been conducted to rationalize the mechanism and regioselectivity, providing insights into the selective functionalization of isoprene and N-functionalization of indazoles.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Stereoselective Synthesis of Cyclobutanes by Contraction of Pyrrolidines

Chunngai Hui et al.

Summary: This report presents a contractive synthesis of multisubstituted cyclobutanes from readily accessible pyrrolidines using iodonitrene chemistry. The stereospecific synthesis of cyclobutanes through a radical pathway mediated by a nitrogen extrusion process is described, resulting in the successful preparation of unprecedented unsymmetrical spirocyclobutanes, as well as a concise, formal synthesis of the cytotoxic natural product Piperarborenine B.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Medicinal

US FDA Approved Drugs from 2015-June 2020: A Perspective

Priyadeep Bhutani et al.

Summary: This study compiled and analyzed 245 drugs approved by the U.S. FDA from 2015 to June 2020, focusing on cancer, infectious diseases, neurological conditions, and genetic, metabolic, cardiovascular disorders. The analysis also looked at the structural, elemental, and functional group diversity among the approved drugs, as well as drug-likeness for the approved drugs.

JOURNAL OF MEDICINAL CHEMISTRY (2021)

Article Multidisciplinary Sciences

Skeletal editing through direct nitrogen deletion of secondary amines

Sean H. Kennedy et al.

Summary: This reaction successfully removes nitrogen from organic molecules, promoting carbon-carbon coupling reactions and expanding the accessible chemical space.

NATURE (2021)

Article Chemistry, Multidisciplinary

N-Atom Deletion in Nitrogen Heterocycles

Haitao Qin et al.

Summary: The study introduces a versatile and novel method for excising N-atoms from N-heterocycles, which can be used to synthesize various cyclic products using readily available substrates. Additionally, examples are provided for nitrogen excision from natural products and synthesis of chiral O-heterocycles.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Carbon Atom Insertion into Pyrroles and Indoles Promoted by Chlorodiazirines

Balu D. Dherange et al.

Summary: This study presents a reaction for selectively generating 3-arylpyridine and quinoline motifs by inserting aryl carbynyl cation equivalents into pyrrole and indole cores. The use of α-chlorodiazirines as thermal precursors allows for a modification of the traditional protocol to directly afford these compounds. Selectivity based on pyrrole substitution patterns is examined, with a predictive model proposed based on steric effects.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Multidisciplinary Sciences

Photomediated ring contraction of saturated heterocycles

Justin Jurczyk et al.

Summary: A visible light-mediated ring contraction of alpha-acylated saturated heterocycles is described, challenging the paradigm of traditional ring contractions and successfully applied to late-stage remodeling of pharmaceutical derivatives, peptides, and sugars.

SCIENCE (2021)

Article Chemistry, Multidisciplinary

Deconstructive Reorganization: De Novo Synthesis of Hydroxylated Benzofuran

Ling Zhang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Unusual Skeletal Reorganization of Oxetanes for the Synthesis of 1,2-Dihydroquinolines

Guannan Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Review Biochemistry & Molecular Biology

A Review on Recent Advances in Nitrogen-Containing Molecules and Their Biological Applications

Nagaraju Kerru et al.

MOLECULES (2020)

Article Chemistry, Multidisciplinary

Ligand-Regulated Regiodivergent Hydrosilylation of Isoprene under Iron Catalysis

Chang-Sheng Kuai et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Review Chemistry, Multidisciplinary

Prescribed drugs containing nitrogen heterocycles: an overview

Majid M. Heravi et al.

RSC ADVANCES (2020)

Review Chemistry, Multidisciplinary

Beckmann rearrangement catalysis: a review of recent advances

Kamalpreet Kaur et al.

NEW JOURNAL OF CHEMISTRY (2020)

Article Multidisciplinary Sciences

Skeletal reorganization divergence of N-sulfonyl ynamides

Linwei Zeng et al.

NATURE COMMUNICATIONS (2020)

Article Chemistry, Multidisciplinary

Catalytic Prenylation and Reverse Prenylation of Indoles with Isoprene: Regioselectivity Manipulation through Choice of Metal Hydride

Yan-Cheng Hu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Ni-Catalyzed Enantioselective Intermolecular Hydroamination of Branched 1,3-Dienes Using Primary Aliphatic Amines

Gael Tran et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

Organic synthesis provides opportunities to transform drug discovery

David C. Blakemore et al.

NATURE CHEMISTRY (2018)

Article Chemistry, Multidisciplinary

Direct Photocatalytic Synthesis of Medium-Sized Lactams by C-C Bond Cleavage

Na Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Medicinal

The Necessary Nitrogen Atom: A Versatile High-Impact Design Element for Multiparameter Optimization

Lewis D. Pennington et al.

JOURNAL OF MEDICINAL CHEMISTRY (2017)

Article Chemistry, Multidisciplinary

Intermolecular Hydroamination of 1,3-Dienes To Generate Homoallylic Amines

Xiao-Hui Yang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Chemistry, Multidisciplinary

Enantioselective Intermolecular Addition of Aliphatic Amines to Acyclic Dienes with a Pd-PHOX Catalyst

Nathan J. Adamson et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Chemistry, Multidisciplinary

Rhodium-Catalyzed Hydrofunctionalization: Enantioselective Coupling of Indolines and 1,3-Dienes

Xiao-Hui Yang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Review Chemistry, Multidisciplinary

Ring-Expansion Reactions in the Synthesis of Macrocycles and Medium-Sized Rings

James R. Donald et al.

CHEMISTRY-A EUROPEAN JOURNAL (2017)

Review Chemistry, Multidisciplinary

Recent applications of the 1,2-carbon atom migration strategy in complex natural product total synthesis

Xiao-Ming Zhang et al.

CHEMICAL SOCIETY REVIEWS (2017)

Article Chemistry, Multidisciplinary

Utility of Ligand Effect in Homogenous Gold Catalysis: Enabling Regiodivergent π-Bond-Activated Cyclization

Dong Ding et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

A General Catalytic Hydroamidation of 1,3-Dienes: Atom-Efficient Synthesis of N-Allyl Heterocycles, Amides, and Sulfonamides

Debasis Banerjee et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Chemistry, Multidisciplinary

Sc(OTf)3-Catalyzed Bicyclization of o-Alkynylanilines with Aldehydes: Ring-Fused 1,2-Dihydroquinolines

Can Zhu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Chemistry, Multidisciplinary

Intermolecular Hydroamination of 1,3-Dienes Catalyzed by Bis(phosphine)carbodicarbene-Rhodium Complexes

Matthew J. Goldfogel et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Chemistry, Organic

Adventures in Ring-Contraction Reactions

Luiz F. Silva

SYNLETT (2014)

Article Chemistry, Multidisciplinary

Ring-Contraction Strategy for the Practical, Scalable, Catalytic Asymmetric Synthesis of Versatile gamma-Quaternary Acylcyclopentenes

Allen Y. Hong et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

Review Chemistry, Multidisciplinary

Semipinacol Rearrangement in Natural Product Synthesis

Zhen-Lei Song et al.

CHEMICAL REVIEWS (2011)

Article Chemistry, Multidisciplinary

A highly efficient and selective Au-I-catalyzed tandem synthesis of diversely substituted pyrrolo[1,2-a]quinolines in aqueous media

Xin-Yuan Liu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

Article Chemistry, Multidisciplinary

Tropene derivatives by sequential intermolecular and transannular, intramolecular palladium-catalyzed hydroamination of cycloheptatriene

Norio Sakai et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

Article Chemistry, Organic

On the mechanism of the Skraup-Doebner-Von Miller quinoline synthesis

SE Denmark et al.

JOURNAL OF ORGANIC CHEMISTRY (2006)

Article Chemistry, Multidisciplinary

A general nickel-catalyzed hydroamination of 1,3-dienes by alkylamines: Catalyst selection, scope, and mechanism

J Pawlas et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2002)

Article Chemistry, Multidisciplinary

Palladium-catalyzed hydroamination of 1,3-dienes:: A colorimetric assay and enantioselective additions

O Löber et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2001)