4.7 Article

Asymmetric synthesis of dihydrocarbazoles through a Friedel-Crafts alkylation/annulation sequential reaction of indoles

Related references

Note: Only part of the references are listed.
Article Chemistry, Multidisciplinary

Feng Ligand: Privileged Chiral Ligand in Asymmetric Catalysis

Ming-Yang Wang et al.

Summary: Feng ligand, a conformationally flexible and C-2-symmetric privileged chiral ligand, has shown tremendous success in asymmetric catalysis, versatile coordination chemistry, and diverse areas of catalysis. Its ability to provide an excellent chiral environment challenges the conventional idea of rigid structures in chiral ligand design.

CHINESE JOURNAL OF CHEMISTRY (2021)

Article Chemistry, Physical

Rhodium(II)-Catalyzed Regioselective Remote C-H Alkylation of Protic Indoles

Lingheng Kong et al.

Summary: The regioselective coupling of NH indoles with diazo compounds using dimeric Rh(II) complexes as catalysts demonstrates selectivity towards C(6) or C(7) positions depending on the structure of the indoles. Mechanistic studies reveal that hydrogen-bonding directing effect plays a crucial role in determining the regioselectivity, with C-C bond formation proceeding through Friedel-Crafts-type attack. This work highlights the challenges and opportunities in controlling regioselectivity in reactions involving arene C-H bonds.

ACS CATALYSIS (2021)

Article Chemistry, Organic

Copper-Catalyzed Annulation of Indolyl α-Diazocarbonyl Compounds Leads to Structurally Rearranged Carbazoles

Sima Alavi et al.

Summary: The study investigates the rearrangement of indolyl alpha-diazocarbonyl compounds under metal catalysis, and reveals the effects of catalyst and substituents on the selectivity of the rearrangement process.

ORGANIC LETTERS (2021)

Article Chemistry, Multidisciplinary

Asymmetric catalytic 1,3-dipolar cycloaddition of α-diazoesters for synthesis of 1-pyrazoline-based spirochromanones and beyond

Peng Zhao et al.

Summary: In this study, a highly enantioselective 1,3-dipolar cycloaddition of alpha-substituted diazoesters with exocyclic enones was achieved using a chiral scandium(III)/N,N'-dioxide complex as the catalyst. The protocol provided an efficient route to optically active products with good outcomes, including up to 97% yield and 98% ee with >95:5 dr. Additionally, enantioenriched 2-pyrazoline-based spirochromanones were accessible by switching alpha-substituted diazoesters to alpha-diazoacetates. Further specific transformations of chiral pyrazoline-based spiro-compounds to spirocyclopropane derivatives were also disclosed in the study.

SCIENCE CHINA-CHEMISTRY (2021)

Review Chemistry, Physical

Ternary Catalysis: A Stepping Stone toward Multicatalysis

Shashank P. Sancheti et al.

ACS CATALYSIS (2020)

Review Multidisciplinary Sciences

Chiral N,N′-dioxide and their metal complexes in asymmetric catalysis

Weidi Cao et al.

CHINESE SCIENCE BULLETIN-CHINESE (2020)

Article Chemistry, Organic

Sodium-Catalyzed Friedel-Crafts Reactions and Mechanistic Insight

Kelsey M. Mesa et al.

ORGANIC LETTERS (2019)

Article Chemistry, Organic

Total Syntheses of Pleiocarpamine, Normavacurine, and C-Mavacurine

Keigo Sato et al.

ORGANIC LETTERS (2019)

Review Chemistry, Multidisciplinary

Indole Alkaloid Synthesis Facilitated by Photoredox Catalytic Radical Cascade Reactions

Xiao-Yu Liu et al.

ACCOUNTS OF CHEMICAL RESEARCH (2019)

Review Chemistry, Multidisciplinary

Different Strategies for Designing Dual-Catalytic Enantioselective Processes: From Fully Cooperative to Non-cooperative Systems

Filippo Romiti et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

Tryptamine Synthesis by Iron Porphyrin Catalyzed C-H Functionalization of Indoles with Diazoacetonitrile

Katharina J. Hock et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Chemistry, Organic

Cascade reaction based synthetic strategies targeting biologically intriguing indole polycycles

Maria Gessica Ciulla et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2019)

Review Biochemistry & Molecular Biology

Catalytic asymmetric dearomatization (CADA) reaction-enabled total synthesis of indole-based natural products

Chao Zheng et al.

NATURAL PRODUCT REPORTS (2019)

Article Chemistry, Multidisciplinary

Chiral Amino Acids-Derived Catalysts and Ligands

Xiaohua Liu et al.

CHINESE JOURNAL OF CHEMISTRY (2018)

Article Chemistry, Multidisciplinary

Asymmetric Synthesis of Tetrahydroindolizines by Bimetallic Relay Catalyzed Cycloaddition of Pyridinium Ylides

Dong Zhang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Review Chemistry, Multidisciplinary

Metamorphosis of cycloalkenes for the divergent total synthesis of polycyclic indole alkaloids

Zhengren Xu et al.

CHEMICAL SOCIETY REVIEWS (2018)

Article Chemistry, Multidisciplinary

Bimetallic Rhodium(II)/Indium(III) Relay Catalysis for Tandem Insertion/Asymmetric Claisen Rearrangement

Yushuang Chen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Review Multidisciplinary Sciences

Recent progress in organocatalytic asymmetric total syntheses of complex indole alkaloids

Jin Song et al.

NATIONAL SCIENCE REVIEW (2017)

Review Chemistry, Multidisciplinary

Transition-Metal-Catalyzed Cross-Couplings through Carbene Migratory Insertion

Ying Xia et al.

CHEMICAL REVIEWS (2017)

Review Chemistry, Multidisciplinary

Asymmetric Cycloaddition and Cyclization Reactions Catalyzed by Chiral N,N′-Dioxide-Metal Complexes

Xiaohua Liu et al.

ACCOUNTS OF CHEMICAL RESEARCH (2017)

Article Chemistry, Multidisciplinary

Selective Synthesis of Six Products from a Single Indolyl α-Diazocarbonyl Precursor

Michael J. James et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Review Chemistry, Multidisciplinary

Homologation Reaction of Ketones with Diazo Compounds

Nuno R. Candeias et al.

CHEMICAL REVIEWS (2016)

Article Chemistry, Multidisciplinary

Enantioselective Palladium-Catalyzed C-H Functionalization of Indoles Using an Axially Chiral 2,2′-Bipyridine Ligand

Xiang Gao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Review Chemistry, Multidisciplinary

Modern Organic Synthesis with α-Diazocarbonyl Compounds

Alan Ford et al.

CHEMICAL REVIEWS (2015)

Article Chemistry, Organic

Catalytic Asymmetric Reactions by Metal and Chiral Phosphoric Acid Sequential Catalysis

Ze-Peng Yang et al.

JOURNAL OF ORGANIC CHEMISTRY (2014)

Article Chemistry, Multidisciplinary

Total Synthesis of the Akuammiline Alkaloid Picrinine

Joel M. Smith et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Chemistry, Organic

Chiral N,N′-dioxide ligands: synthesis, coordination chemistry and asymmetric catalysis

Xiaohua Liu et al.

ORGANIC CHEMISTRY FRONTIERS (2014)

Review Chemistry, Multidisciplinary

Novel Multicomponent Reactions via Trapping of Protic Onium Ylides with Electrophiles

Xin Guo et al.

ACCOUNTS OF CHEMICAL RESEARCH (2013)

Review Chemistry, Multidisciplinary

Asymmetric Relay Catalysis Reaction Consisting of Metal Complex and Chiral Phosphoric Acids

Wu Xiang et al.

ACTA CHIMICA SINICA (2013)

Article Chemistry, Multidisciplinary

Enantioselective Friedel-Crafts alkylation for synthesis of 2-substituted indole derivatives

Yulong Zhang et al.

CHEMICAL COMMUNICATIONS (2013)

Article Chemistry, Organic

Diazoacetoacetate Enones for the Synthesis of Diverse Natural Product-like Scaffolds

Charles S. Shanahan et al.

ORGANIC LETTERS (2013)

Review Chemistry, Multidisciplinary

Transition-Metal-Catalyzed Enantioselective Heteroatom-Hydrogen Bond Insertion Reactions

Shou-Fei Zhu et al.

ACCOUNTS OF CHEMICAL RESEARCH (2012)

Review Chemistry, Multidisciplinary

Chiral N,N′-Dioxides: New Ligands and Organocatalysts for Catalytic Asymmetric Reactions

Xiaohua Liu et al.

ACCOUNTS OF CHEMICAL RESEARCH (2011)

Article Chemistry, Applied

Iron-Catalyzed C?H Fuctionalization of Indoles

Yan Cai et al.

ADVANCED SYNTHESIS & CATALYSIS (2011)

Article Chemistry, Multidisciplinary

Diastereoselectively Switchable Enantioselective Trapping of Carbamate Ammonium Ylides with Imines

Jun Jiang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

Article Chemistry, Multidisciplinary

Redox-Neutral Indole Annulation Cascades

Michael C. Haibach et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

Article Chemistry, Organic

A New Type of Monoterpenoid Indole Alkaloid Precursor from Alstonia rostrata

Xiang-Hai Cai et al.

ORGANIC LETTERS (2011)

Article Chemistry, Multidisciplinary

Rhodium-Catalyzed [3+2] Annulation of Indoles

Yajing Lian et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

Article Chemistry, Multidisciplinary

Total Synthesis of the Akuammiline Alkaloid (±)-Vincorine

Min Zhang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

Review Biochemistry & Molecular Biology

Chemistry and biology of monoterpene indole alkaloid biosynthesis

Sarah E. O'Connor et al.

NATURAL PRODUCT REPORTS (2006)

Review Chemistry, Multidisciplinary

Reserpine: A challenge for total synthesis of natural products

FE Chen et al.

CHEMICAL REVIEWS (2005)