Ni-catalyzed carbamoylation of unactivated alkenes for stereoselective construction of six-membered lactams

Article Chemistry, Multidisciplinary

Enantioselective Synthesis of α-Alkenylated γ-Lactam Enabled by Ni-Catalyzed 1,4-Arylcarbamoylation of 1,3-Dienes

Feng He et al.

Summary: This article reports a new method for the synthesis of chiral quaternary alpha-alkenylated pyrrolidinones through nickel-catalyzed asymmetric 1,4-arylcarbamoylation. This method has significant importance in organic synthesis.

CCS CHEMISTRY (2023)

添加到收藏夹

Article Chemistry, Organic

8-Quinolinyl Oxazoline: Ligand Exploration in Enantioselective Ni-Catalyzed Reductive Carbamoyl-Alkylation of Alkene to Access the Chiral Oxindoles

Baixue Luan et al.

Summary: Chiral ligands, especially 8-Quinox ligands, have a significant impact on transition-metal-catalyzed enantioselective transformations. This study presents a method for the Ni-catalyzed enantioselective reductive carbamoyl-alkylation, using 8-Quinox ligands, to efficiently access enantioenriched oxindoles.

SYNLETT (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Nickel-Catalyzed Enantioselective Reductive Alkyl-Carbamoylation of Internal Alkenes

Xianqing Wu et al.

Summary: In this study, Ni-catalyzed enantioselective reductive dicarbofunctionalization of internal alkenes with alkyl iodides was used to synthesize chiral pyrrolidinones with vicinal stereogenic centers. The newly developed (1-Nap)Quinim played a critical role in the formation of two contiguous stereocenters with high yield, enantioselectivity, and diastereoselectivity. This catalytic system also improved the yield and enantioselectivity in the synthesis of alpha,alpha-dialkylated gamma-lactams.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Nickel-Catalyzed Asymmetric Reductive Carbo-Carboxylation of Alkenes with CO2

Xiao-Wang Chen et al.

Summary: The asymmetric reductive carbo-carboxylation of alkenes via nickel catalysis provides an efficient method for the synthesis of carboxylic acids with mild reaction conditions, wide substrate scope, and good selectivity. This approach opens up a new avenue for the total synthesis of chiral natural products using CO2.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantioselective Reductive Divinylation of Unactivated Alkenes by Nickel-Catalyzed Cyclization Coupling Reaction

Jin-Bao Qiao et al.

Summary: The developed method provides a new tool for the synthesis of chiral cyclic molecules with high selectivity from different substrates, applicable for the synthesis of biologically active compounds.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

添加到收藏夹

Article Chemistry, Organic

Synthesis of 3,3-Dialkyl-Substituted Isoindolinones Enabled by Nickel-Catalyzed Reductive Dicarbofunctionalization of Enamides

Ke Fang et al.

Summary: A novel nickel-catalyzed reaction method for the synthesis of 3,3-dialkyl-substituted isoindolinone frameworks from unactivated alkyl iodides and 1,1-disubstituted enamides has been reported. The method exhibits good functional group tolerance and enantioselectivity through the use of commercially available chiral Bn-Biox ligand.

ORGANIC LETTERS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Palladium-catalyzed asymmetric carbamoyl-carbonylation of alkenes

Ziwen Feng et al.

Summary: The unprecedented palladium-catalyzed asymmetric carbamoyl-carbonylation of tethered alkenes with CO and alcohols provides efficient access to oxindoles and gamma-lactams bearing beta-carbonyl substituted quaternary carbons in good yields with excellent chemo-, regio-, and enantioselectivity. The gram-scale synthetic capability and facile transformations of the products further demonstrate the practicality of this reaction for synthesizing chiral spirooxindole and other functional molecules.

SCIENCE CHINA-CHEMISTRY (2021)

添加到收藏夹

Review Chemistry, Organic

Recent Advances on the Synthesis of β-Lactams by Involving Carbon Monoxide

Peng Wang et al.

Summary: This paper reviews the recent research on the carbonylation of different substrates with CO to synthesize beta-lactams, highlighting the importance and future prospects of this strategy in the field of organic chemistry.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Organic

Facile Preparation of Aryl C-Glycosides by Nickel-Catalyzed Reductive Coupling of Glycosyl Halides with Aryl Halides

Yuren Sun et al.

Summary: The method developed allows for the preparation of C-aryl glycosides via mild Ni/bipyridine-catalyzed reductive arylation of C(1)-glycosyl halides with electron-deficient aryl bromides, achieving moderate to high alpha-selectivities. A broad range of aryl halides, including electron-rich aryl iodides, can be used to yield C-aryl glycosides in 40% to 5% yields. The method can be scaled up on a gram scale by lowering the loading of nickel catalyst to 2 mol%.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2021)

添加到收藏夹

Review Chemistry, Organic

Recent advances in transition metal-catalyzed reactions of carbamoyl chlorides

Mohini Shrestha et al.

Summary: This review article summarizes the development of carbamoyl chlorides as synthons for various amide-containing molecules and heterocycles in transition metal-catalyzed reactions. It highlights the advancements and applications of carbamoyl chlorides in organic framework synthesis, as well as briefly discusses the chemical behavior of their structural analogs.

ORGANIC CHEMISTRY FRONTIERS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Nickel-catalyzed asymmetric reductive aryl-allylation of unactivated alkenes

Zhiyang Lin et al.

Summary: The nickel-catalyzed asymmetric reductive aryl-allylation reaction described in this study shows high stereo-selectivity in the synthesis of chiral compounds containing homoallyl substitution.

CHEMICAL SCIENCE (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Nickel-Catalyzed Asymmetric Reductive 1,2-Carboamination of Unactivated Alkenes

Jun He et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Construction of Quaternary Carbon Center by Catalytic Asymmetric Alkylation of 3-Arylpiperidin-2-ones Under Phase-Transfer Conditions

Tomoaki Inukai et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Nickel/Photo-Cocatalyzed Asymmetric Acyl-Carbamoylation of Alkenes

Pei Fan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

添加到收藏夹

Review Chemistry, Organic

Ni-Catalyzed Reductive Difunctionalization of Alkenes

Yuanyuan Ping et al.

SYNTHESIS-STUTTGART (2020)

添加到收藏夹

Article Chemistry, Physical

Asymmetric Synthesis of β-Lactam via Palladium-Catalyzed Enantioselective Intramolecular C(sp3)-H Amidation

Hua-Rong Tong et al.

ACS CATALYSIS (2020)

添加到收藏夹

Article Chemistry, Physical

Nickel-Catalyzed Enantioselective Carbamoyl Iodination: A Surrogate for Carbamoyl Iodides

Austin D. Marchese et al.

ACS CATALYSIS (2020)

添加到收藏夹

Review Chemistry, Multidisciplinary

Nickel-CatalyzedDicarbofunctionalization of Alkenes†

Yun-Cheng Luo et al.

CHINESE JOURNAL OF CHEMISTRY (2020)

添加到收藏夹

Article Chemistry, Organic

Nickel-Catalyzed Asymmetric Cross-Electrophile Coupling Reactions

Youxiang Jin et al.

SYNLETT (2020)

添加到收藏夹

Article Chemistry, Physical

Nickel-Catalyzed Enantioselective Reductive Cross-Coupling Reactions

Kelsey E. Poremba et al.

ACS CATALYSIS (2020)

添加到收藏夹

Article Chemistry, Physical

Nickel-Catalyzed Dicarbofunctionalization of Alkenes

Xiaoxu Qi et al.

ACS CATALYSIS (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Quinim: A New Ligand Scaffold Enables Nickel-Catalyzed Enantioselective Synthesis of α-Alkylated γ-Lactam

Xianqing Wu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

添加到收藏夹

Article Chemistry, Organic

Stereoselective Construction of γ-Lactams via Copper-Catalyzed Borylacylation

Alexa Torelli et al.

ORGANIC LETTERS (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Carbamoyl Fluoride-Enabled Enantioselective Ni-Catalyzed Carbocarbamoylation of Unactivated Alkenes

Yue Li et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Nickel-catalyzed enantioselective reductive carbo-acylation of alkenes

Yun Lan et al.

COMMUNICATIONS CHEMISTRY (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Nickel-Catalyzed Asymmetric Reductive Arylalkylation of Unactivated Alkenes

Youxiang Jin et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Palladium-Catalyzed Construction of Quaternary Stereocenters by Enantioselective Arylation of -Lactams with Aryl Chlorides and Bromides

Carina I. Jette et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Ruthenium(II)-Catalyzed Enantioselective γ-Lactams Formation by Intramolecular C-H Amidation of 1,4,2-Dioxazol-5-ones

Qi Xing et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

添加到收藏夹

Article Chemistry, Organic

Enantioselective palladium-catalyzed C(sp2)-H carbamoylation

Wenfeng Dong et al.

TETRAHEDRON (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Iridium-Catalyzed Enantioselective C(sp3)-H Amidation Controlled by Attractive Noncovalent Interactions

Hao Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Highly Enantioselective Cross-Electrophile Aryl-Alkenylation of Unactivated Alkenes

Zhi-Xiong Tian et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

添加到收藏夹

Article Chemistry, Physical

Ni-Catalyzed Regio- and Enantioselective Domino Reductive Cyclization: One-Pot Synthesis of 2,3-Fused Cyclopentannulated Indolines

Yuanyuan Ping et al.

ACS CATALYSIS (2019)

添加到收藏夹

Review Chemistry, Multidisciplinary

Mechanisms of Nickel-Catalyzed Cross-Coupling Reactions

Justin B. Diccianni et al.

TRENDS IN CHEMISTRY (2019)

添加到收藏夹

Article Chemistry, Physical

Asymmetric formation of γ-lactams via C-H amidation enabled by chiral hydrogen-bond-donor catalysts

Yoonsu Park et al.

NATURE CATALYSIS (2019)

添加到收藏夹

Article Chemistry, Inorganic & Nuclear

Baldwin-Type Rules for Metal-Controlled Intramolecular Migratory Insertions. A Computational Study of Ni, Pd, and Pt Case

Bela Fiser et al.

ORGANOMETALLICS (2018)

添加到收藏夹

Article Chemistry, Organic

Generation of all carbon quaternary stereocenters at the C-3 carbon of piperidinones and pyrrolidinones and its application in natural product total synthesis

Ganesh Pandey et al.

TETRAHEDRON (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantioselective Intramolecular Copper-Catalyzed Borylacylation

Andrew Whyte et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Ni-Catalyzed Enantioselective Reductive Diarylation of Activated Alkenes by Domino Cyclization/Cross-Coupling

Kuai Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

添加到收藏夹

Article Multidisciplinary Sciences

Catalytic enantioconvergent coupling of secondary and tertiary electrophiles with olefins

Zhaobin Wang et al.

NATURE (2018)

添加到收藏夹

Article Chemistry, Applied

Organocatalytic Asymmetric Synthesis of 3,3-Disubstituted 3,4-Dihydro-2-quinolones

Soumendranath Mukhopadhyay et al.

ADVANCED SYNTHESIS & CATALYSIS (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Synthesis of β-Lactams by Palladium(0)-Catalyzed C(sp3)-H Carbamoylation

David Dailler et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Ni-Catalyzed Enantioselective C-Acylation of α-Substituted Lactams

Masaki Hayashi et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

添加到收藏夹

Review Chemistry, Organic

Modern advances in heterocyclic chemistry in drug discovery

Alexandria P. Taylor et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2016)

添加到收藏夹

Review Chemistry, Multidisciplinary

Catalytic Enantioselective Construction of Quaternary Stereocenters: Assembly of Key Building Blocks for the Synthesis of Biologically Active Molecules

Yiyang Liu et al.

ACCOUNTS OF CHEMICAL RESEARCH (2015)

添加到收藏夹

Article Chemistry, Organic

Asymmetric Michael Addition Reaction of α-Aryl-Substituted Lactams Catalyzed by Chiral Quaternary Ammonium Salts Derived from Cinchona Alkaloids: A New Short Synthesis of (+)-Mesembrine

Shiori Nunokawa et al.

SYNLETT (2015)

添加到收藏夹

Article Chemistry, Organic

Nickel-catalyzed reductive coupling of alkyl halides with other electrophiles: concept and mechanistic considerations

Jun Gu et al.

ORGANIC CHEMISTRY FRONTIERS (2015)

添加到收藏夹

Article Chemistry, Multidisciplinary

Access to β-Lactams by Enantioselective Palladium(0)-Catalyzed C(sp3)-H Alkylation

Julia Pedroni et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

添加到收藏夹

Review Chemistry, Multidisciplinary

Chemical Synthesis of β-Lactams: Asymmetric Catalysis and Other Recent Advances

Cody Ross Pitts et al.

CHEMICAL REVIEWS (2014)

添加到收藏夹

Review Chemistry, Multidisciplinary

Metal-Catalyzed Reductive Coupling Reactions of Organic Halides with Carbonyl-Type Compounds

Toni Moragas et al.

CHEMISTRY-A EUROPEAN JOURNAL (2014)

添加到收藏夹

Article Chemistry, Medicinal

Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among US FDA Approved Pharmaceuticals

Edon Vitaku et al.

JOURNAL OF MEDICINAL CHEMISTRY (2014)

添加到收藏夹

Article Chemistry, Organic

Cross-Electrophile Coupling: Principles of Reactivity and Selectivity

Daniel A. Everson et al.

JOURNAL OF ORGANIC CHEMISTRY (2014)

添加到收藏夹

Review Chemistry, Organic

Recent progress towards transition metal-catalyzed synthesis of γ-lactams

Long-Wu Ye et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2014)

添加到收藏夹

Article Chemistry, Multidisciplinary

Catalytic Asymmetric Reductive Acyl Cross-Coupling: Synthesis of Enantioenriched Acyclic α,α-Disubstituted Ketones

Alan H. Cherney et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

添加到收藏夹

Article Chemistry, Multidisciplinary

Diaminophosphine Oxide Ligand Enabled Asymmetric Nickel-Catalyzed Hydrocarbamoylations of Alkenes

Pavel A. Donets et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

添加到收藏夹

Review Chemistry, Multidisciplinary

Recent advances in organocatalytic methods for the synthesis of disubstituted 2-and 3-indolinones

Renato Dalpozzo et al.

CHEMICAL SOCIETY REVIEWS (2012)

添加到收藏夹

Review Chemistry, Multidisciplinary

Advances in the Chemistry of Tetrahydroquinolines

Vellaisamy Sridharan et al.

CHEMICAL REVIEWS (2011)

添加到收藏夹

Article Chemistry, Organic

Enantioselective synthesis of 3,3-disubstituted oxindoles through Pd-catalyzed cyanoamidation

Yoshimmi Yasui et al.

ORGANIC LETTERS (2008)

添加到收藏夹

Article Chemistry, Organic

Enantioselective synthesis of 3,3-disubstituted piperidine derivatives by enolate dialkylation of phenylglycinol-derived oxazolopiperidone lactams

Mercedes Amat et al.

JOURNAL OF ORGANIC CHEMISTRY (2007)

添加到收藏夹

Review Chemistry, Organic

Recent advances in the synthesis of piperidones and piperidines

PM Weintraub et al.

TETRAHEDRON (2003)

添加到收藏夹

Review Chemistry, Organic

Chiral non-racemic bicyclic lactams. Auxiliary-based asymmetric reactions

MD Groaning et al.

TETRAHEDRON (2000)

添加到收藏夹

Ni-catalyzed carbamoylation of unactivated alkenes for stereoselective construction of six-membered lactams

相关参考文献

导出引文

分享论文