☆ 4.8 Letter

Catalytic Asymmetric Allylic Substitution/Isomerization with Central Chirality Transposition

ORGANIC LETTERS (2022)

Related references

Note: Only part of the references are listed.

Article Chemistry, Multidisciplinary

Chiral Bronsted Acid Catalyzed Enantioconvergent Synthesis of Chiral Tetrahydrocarbazoles with Allenylsilanes from Racemic Indolylmethanols

Shigenobu Umemiya et al.

Summary: An efficient method for synthesizing chiral tetrahydrocarbazoles with an allene moiety was developed using enantioconvergent substitution reaction catalyzed by a chiral phosphoric acid. The reaction between racemic indolylmethanols and N-methylpyrrole in the presence of SPINOL-derived chiral phosphoric acid yielded the desired chiral tetrahydrocarbazoles with allenylsilanes in high yields and enantioselectivities.

CHEMISTRY LETTERS (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Organocatalytic discrimination of non-directing aryl and heteroaryl groups: enantioselective synthesis of bioactive indole-containing triarylmethanes

Qiaolin Yan et al.

Summary: This study demonstrates excellent enantioselection between aryl and heteroaryl groups using a robust organocatalytic system. By studying the versatile 2-indole imine methide, highly enantioenriched indole-containing triarylmethanes were synthesized, and the mechanism was explored through control experiments and kinetic studies. Preliminary biological studies also indicate the potential of these compounds for anticancer and antiviral drug development.

CHEMICAL SCIENCE (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Regio- and Enantioselective (3+3) Cycloaddition of Nitrones with 2-Indolylmethanols Enabled by Cooperative Organocatalysis

Tian-Zhen Li et al.

Summary: The regio- and enantioselective (3+3) cycloaddition of nitrones with 2-indolylmethanols was successfully achieved through the cooperative catalysis of hexafluoroisopropanol (HFIP) and chiral phosphoric acid (CPA). This approach resulted in the synthesis of indole-fused six-membered heterocycles with high yields, excellent enantioselectivities, and exclusive regiospecificity. The role of the cocatalyst HFIP in helping CPA control the reactivity and enantioselectivity of the reaction was elucidated through theoretical calculations, demonstrating a new mode of cooperative catalysis.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Add to Collection

Review Chemistry, Multidisciplinary

Enantioconvergent Substitution Reactions of Racemic Electrophiles by Organocatalysis

Jun Kikuchi et al.

Summary: The development of enantioselective catalysis using organocatalysts has become a prominent research field, with recent advancements in enantioconvergent substitution reactions despite challenges.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Tandem Iridium Catalysis as a General Strategy for Atroposelective Construction of Axially Chiral Styrenes

Jie Wang et al.

Summary: This study presents a novel approach for the synthesis of axially chiral styrenes through tandem iridium catalysis. The method allows for efficient and selective preparation of chiral ligands needed for asymmetric synthesis.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Add to Collection

Article Multidisciplinary Sciences

Organocatalytic enantioselective dearomatization of thiophenes by 1,10-conjugate addition of indole imine methides

Xingguang Li et al.

Summary: Catalytic asymmetric dearomatization is a powerful method for constructing diverse chiral cyclic molecules from readily available arenes. The authors demonstrate an organocatalytic enantioselective dearomatization of substituted thiophenes in the context of a rare remote asymmetric 1,10-conjugate addition, showcasing excellent remote chemo-, regio-, and stereocontrol with chiral phosphoric acid catalysis. This protocol can be extended to the asymmetric dearomatization of other heteroarenes and involves hydrogen bonding for selectivity control as demonstrated by control experiments and DFT calculations.

NATURE COMMUNICATIONS (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Ir-catalyzed Sequential Asymmetric Allylic Substitution/Olefin Isomerization for the Synthesis of Axially Chiral Compounds

Qing-Ru Zhao et al.

Summary: An efficient strategy was developed to access a series of axially chiral styrenes by iridium-catalyzed allylic substitution and central-to-axial chirality transfer via olefin isomerization. The method provides a broad range of axially chiral styrenes with moderate to excellent yields and enantioselectivity, offering a powerful tool in asymmetric organic synthesis.

ACTA CHIMICA SINICA (2021)

Add to Collection

Review Chemistry, Multidisciplinary

Organocatalytic Asymmetric Synthesis of Indole-Based Chiral Heterocycles: Strategies, Reactions, and Outreach

Yu-Chen Zhang et al.

ACCOUNTS OF CHEMICAL RESEARCH (2020)

Add to Collection

Article Chemistry, Organic

Stereospecific Isomerization of Allylic Halides via Ion Pairs with Induced Noncovalent Chirality

Samuel Martinez-Erro et al.

ORGANIC LETTERS (2020)

Add to Collection

Article Chemistry, Multidisciplinary

Organocatalytic Enantioselective Synthesis of Chiral Allenes: Remote Asymmetric 1,8-Addition of Indole Imine Methides

Xingguang Li et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Add to Collection

Article Chemistry, Physical

Catalytic enantioselective synthesis of chiral tetraarylmethanes

Xingguang Li et al.

NATURE CATALYSIS (2020)

Add to Collection

Article Chemistry, Multidisciplinary

Asymmetric allylic substitution-isomerization to axially chiral enamides via hydrogen-bonding assisted central-to-axial chirality transfer

Chao Sun et al.

CHEMICAL SCIENCE (2020)

Add to Collection

Article Chemistry, Multidisciplinary

Catalytic Asymmetric (4+3) Cyclizations of In Situ Generated ortho-Quinone Methides with 2-Indolylmethanols

Meng Sun et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Add to Collection

Article Chemistry, Organic

Cooperative Catalysis-Enabled Asymmetric α-Arylation of Aldehydes Using 2-Indolylmethanols as Arylation Reagents

Meng-Meng Xu et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

Add to Collection

Article Chemistry, Multidisciplinary

Stereospecific 1,3-H Transfer of Indenols Proceeds via Persistent Ion-Pairs Anchored by NH center dot center dot center dot pi Interactions

David M. H. Ascough et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Add to Collection

Article Chemistry, Multidisciplinary

Design and Enantioselective Construction of Axially Chiral Naphthyl-Indole Skeletons

Hong-Hao Zhang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Add to Collection

Review Chemistry, Medicinal

Indoles as therapeutics of interest in medicinal chemistry: Bird's eye view

Navriti Chadha et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2017)

Add to Collection

Article Chemistry, Organic

Substrate-Controlled Regioselective Arylations of 2-Indolylmethanols with Indoles: Synthesis of Bis(indolyl)methane and 3,3'-Bisindole Derivatives

Ying-Ying He et al.

JOURNAL OF ORGANIC CHEMISTRY (2017)

Add to Collection

Article Chemistry, Organic

Enantioselective Direct α-Arylation of Pyrazol-5-ones with 2-Indolylmethanols via Organo-Metal Cooperative Catalysis

Zi-Qi Zhu et al.

ORGANIC LETTERS (2017)

Add to Collection

Article Chemistry, Multidisciplinary

Base-Catalyzed Stereospecific Isomerization of Electron-Deficient Allylic Alcohols and Ethers through Ion-Pairing

Samuel Martinez-Erro et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Add to Collection

Article Chemistry, Organic

Bronsted Acid Catalyzed [3+2]-Cycloaddition of Cyclic Enamides with in Situ Generated 2-Methide-2H-indoles: Enantioselective Synthesis of Indolo[1,2-a]indoles

Kalisankar Bera et al.

ORGANIC LETTERS (2016)

Add to Collection

Review Chemistry, Multidisciplinary

Development and Applications of Disulfonimides in Enantioselective Review Organocatalysis

Thomas James et al.

CHEMICAL REVIEWS (2015)

Add to Collection

Review Chemistry, Multidisciplinary

Stronger Bronsted Acids: Recent Progress

Takahiko Akiyama et al.

CHEMICAL REVIEWS (2015)

Add to Collection

Article Chemistry, Multidisciplinary

Organocatalytic Asymmetric Synthesis of 1,1-Diarylethanes by Transfer Hydrogenation

Zhaobin Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Add to Collection

Article Chemistry, Multidisciplinary

Chiral phosphoramide-catalyzed enantioselective synthesis of 2,3'-diindolylarylmethanes from indol-2-yl carbinols and indoles

Shuai Qi et al.

CHEMICAL COMMUNICATIONS (2014)

Add to Collection

Review Chemistry, Multidisciplinary

Complete Field Guide to Asymmetric BINOL-Phosphate Derived Bronsted Acid and Metal Catalysis: History and Classification by Mode of Activation; Bronsted Acidity, Hydrogen Bonding, Ion Pairing, and Metal Phosphates

Dixit Parmar et al.

CHEMICAL REVIEWS (2014)

Add to Collection

Article Chemistry, Multidisciplinary

Combining NHC-Cu and BrOnsted Base Catalysis: Enantioselective Allylic Substitution/Conjugate Additions with Alkynylaluminum Reagents and Stereospecific Isomerization of the Products to Trisubstituted Allenes

Jennifer A. Dabrowski et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Add to Collection

Article Chemistry, Inorganic & Nuclear

Synthesis of β-CF3 ketones from trifluoromethylated allylic alcohols by ruthenium catalyzed isomerization

Vincent Bizet et al.

JOURNAL OF FLUORINE CHEMISTRY (2013)

Add to Collection

Article Chemistry, Multidisciplinary

Ruthenium-Catalyzed Redox Isomerization of Trifluoromethylated Allylic Alcohols: Mechanistic Evidence for an Enantiospecific Pathway

Vincent Bizet et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

Add to Collection

Review Chemistry, Multidisciplinary

Marine Indole Alkaloids: Potential New Drug Leads for the Control of Depression and Anxiety

Anna J. Kochanowska-Karamyan et al.

CHEMICAL REVIEWS (2010)

Add to Collection

Article Chemistry, Multidisciplinary

Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid

T Akiyama et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2004)

Add to Collection

Article Chemistry, Multidisciplinary

Chiral Bronsted acid-catalyzed direct Mannich reactions via electrophilic activation

D Uraguchi et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2004)

Add to Collection

© Peeref 2019-2024. All rights reserved.