4.8 Article

Iridium-Catalyzed Enantioconvergent Borrowing Hydrogen Annulation of Racemic 1,4-Diols 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

Simultaneous Kinetic Resolution and Asymmetric Induction within a Borrowing Hydrogen Cascade Mediated by a Single Catalyst

Ming Yu Jin et al.

Summary: The mechanistic uniqueness and versatility of borrowing hydrogen catalysis provides an opportunity to investigate the controllability of a cascade reaction, and more importantly, to realize either one or both of chiral recognition and chiral induction simultaneously. In this study, using a robust Ru-catalyst, both kinetic resolution and asymmetric induction were achieved with remarkable levels of efficiency and enantioselectivity, showing the importance of catalyst-substrate pi-pi interactions in realizing stereochemical diversity.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Multidisciplinary

Asymmetric Ruthenium-Catalyzed Hydroalkylation of Racemic Allylic Alcohols for the Synthesis of Chiral Amino Acid Derivatives

Xiaohui Zhang et al.

Summary: The asymmetric hydroalkylation of racemic allylic alcohols has been developed for the synthesis of chiral amino acid derivatives with two remote chiral centers by borrowing hydrogen catalysis. The stereoselectivities are controlled by a single chiral Ru catalyst via a dynamic kinetic asymmetric transformation process and an interesting diastereoselectivity amplification process of the product.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Multidisciplinary

Modular Access to Chiral ?-(Hetero)aryl Amines via Ni/Photoredox-Catalyzed Enantioselective Cross-Coupling

Xiaomin Shu et al.

Summary: We report a general and modular approach for the direct enantioselective alpha-arylation of saturated azacycles and acyclic N-alkyl benzamides via nickel/photoredox dual catalysis. This method requires no oxidants or organometallic reagents, features broad substrate scope and high enantioselectivities, and is applicable to late-stage diversification of medicinally relevant complex molecules.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Review Chemistry, Physical

Borrowing Hydrogen Amination Reactions: A Complex Analysis of Trends and Correlations of the Various Reaction Parameters

Evgeniya Podyacheva et al.

Summary: Borrowing hydrogen or the hydrogen autotransfer amination is a powerful and atom-efficient method for creating single C-N bonds from stable and readily available substrates. This method is considered to be green and is highly efficient in synthesizing complex amines.

ACS CATALYSIS (2022)

Article Chemistry, Multidisciplinary

Stereodivergent Construction of 1,4-Nonadjacent Stereocenters via Hydroalkylation of Racemic Allylic Alcohols Enabled by Copper/Ruthenium Relay Catalysis

Xin Chang et al.

Summary: An unprecedented hydroalkylation reaction catalyzed by Cu/Ru relay was developed, merging the ruthenium-catalyzed asymmetric borrowing-hydrogen reaction with a copper-catalyzed asymmetric Michael addition. This method enables the efficient preparation of highly functionalized delta-hydroxyesters bearing 1,4-nonadjacent stereocenters with high levels of diastereoselectivity and excellent enantioselectivity.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Review Chemistry, Organic

Borrowing Hydrogen and Acceptorless Dehydrogenative Coupling in the Multicomponent Synthesis of N-Heterocycles: A Comparison between Base and Noble Metal Catalysis

Natalie Hofmann et al.

Summary: ADC and HT are powerful tools in the multicomponent formation of N-heterocycles, starting from simple and commercially available reagents. Base metal-catalyzed strategies, using manganese, iron, cobalt, nickel, and copper catalysts, have become increasingly important in recent years. These strategies are highly atom-efficient and environmentally friendly, with no need for further reducing or oxidizing agents.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Organic

Synthesis of Chiral Amines via Asymmetric Hydrogen Borrowing

Kun Wang et al.

Summary: This paper provides a brief summary of the recent progress on asymmetric amination of alcohols to produce chiral amines via the 'hydrogen borrowing' strategy.

SYNLETT (2021)

Review Chemistry, Multidisciplinary

Reducing Challenges in Organic Synthesis with Stereoselective Hydrogenation and Tandem Catalysis

Patrick D. Parker et al.

Summary: Tandem catalysis allows for constructing complex structures quickly from simple building blocks to address diverse challenges. This article focuses on using tandem hydrogenation to prepare complex natural products and presents tandem catalysis involving transfer hydrogenation. Lastly, recent breakthroughs and opportunities for asymmetric hydrogenation are highlighted.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Multidisciplinary

Borrowing Hydrogen for Organic Synthesis

Benjamin G. Reed-Berendt et al.

Summary: Borrowing hydrogen is a process used to diversify the synthetic utility of commodity alcohols by oxidizing alcohols to form reactive carbonyl compounds, which can undergo various transformations before the catalyst regenerates. This method has shown significant advances in recent decades, showcasing the diversity of catalysts available and highlighting the potential for further development.

ACS CENTRAL SCIENCE (2021)

Article Chemistry, Multidisciplinary

Tandem Catalytic Indolization/Enantioconvergent Substitution of Alcohols by Borrowing Hydrogen to Access Tricyclic Indoles

Guoqiang Yang et al.

Summary: An efficient tandem catalysis method has been developed for the direct conversion of alcohol-containing alkynyl anilines to valuable chiral 2,3-fused tricyclic indoles. Highly diastereoselective transformations of the tricyclic indole products also provide efficient access to a diverse array of complex polycyclic indoline compounds.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Catalytic Diastereo- and Enantioconvergent Synthesis of Vicinal Diamines from Diols through Borrowing Hydrogen

Hui-Jie Pan et al.

Summary: This study presents an unprecedented diastereoconvergent synthesis of vicinal diamines from diols, using an economical and redox-neutral process. Efficient and diastereoselective coupling of readily available anilines and 1,2-diols under cooperative ruthenium and Lewis acid catalysis was achieved, along with the first enantioconvergent double amination of racemic 1,2-diols through an effective chiral iridium/phosphoric acid co-catalyzed procedure, leading to practical access to highly valuable enantioenriched vicinal diamines.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Multidisciplinary Sciences

Redox-enabled direct stereoconvergent heteroarylation of simple alcohols

Yongbing Liu et al.

Summary: The study introduces a redox-enabled strategy for the enantioselective coupling of pyrroles with racemic secondary alcohols, providing a significant advantage in economically and efficiently synthesizing high enantiopure compounds.

NATURE COMMUNICATIONS (2021)

Review Chemistry, Multidisciplinary

Pyrrolidine in Drug Discovery: A Versatile Scaffold for Novel Biologically Active Compounds

Giovanna Li Petri et al.

Summary: The five-membered pyrrolidine ring and its derivatives have demonstrated bioactivity with target selectivity for treating human diseases. By comparing the physicochemical parameters of pyrrolidine with the parent aromatic pyrrole and cyclopentane, the influence of steric factors on biological activity was investigated, along with describing the structure-activity relationship of the studied compounds.

TOPICS IN CURRENT CHEMISTRY (2021)

Review Chemistry, Multidisciplinary

Recent advances in transition metal-catalyzed (1,n) annulation using (de)-hydrogenative coupling with alcohols

Sourajit Bera et al.

Summary: This review discusses the synthesis of cyclic compounds using (1,n) annulation reactions, highlighting the progress from 2015 to March 2021. It covers the synthesis of various cyclic structures and their applications, including mechanistic studies, new catalytic methods, and synthetic applications.

CHEMICAL COMMUNICATIONS (2021)

Article Chemistry, Multidisciplinary

Asymmetric Guerbet Reaction to Access Chiral Alcohols

Kun Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Room-Temperature Guerbet Reaction with Unprecedented Catalytic Efficiency and Enantioselectivity

Teng Wei Ng et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Review Chemistry, Multidisciplinary

Control of Absolute Stereochemistry in Transition-Metal-Catalysed Hydrogen-Borrowing Reactions

Timothy Kwok et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

Article Chemistry, Multidisciplinary

Anti-Markovnikov Hydroamination of Racemic Allylic Alcohols to Access Chiral γ-Amino Alcohols

Ruirui Xu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Review Pharmacology & Pharmacy

Pyrrolidine alkaloids and their promises in pharmacotherapy

Muhammad Torequl Islam et al.

ADVANCES IN TRADITIONAL MEDICINE (2020)

Article Chemistry, Multidisciplinary

A hydrogen borrowing annulation strategy for the stereocontrolled synthesis of saturated aza-heterocycles

Anna E. R. Chamberlain et al.

CHEMICAL COMMUNICATIONS (2020)

Article Chemistry, Multidisciplinary

Enantioconvergent alkylation of ketones with racemic secondary alcohols via hydrogen borrowing catalysis

Daniella M. J. Cheang et al.

CHEMICAL COMMUNICATIONS (2020)

Article Chemistry, Multidisciplinary

Stereoconvergent, Redox-Neutral Access to Tetrahydroquinoxalines through Relay Epoxide Opening/Amination of Alcohols

Guangda Xu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Catalytic Asymmetric Synthesis of Cyclohexanes by Hydrogen Borrowing Annulations

Roly J. Armstrong et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Enantioselective Imine Reduction Catalyzed by Phosphenium Ions

Travis Lundrigan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

Catalytic Asymmetric Synthesis of α-Arylpyrrolidines and Benzo-fused Nitrogen Heterocycles

Xi-Jie Dai et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Chemistry, Multidisciplinary

3d-Metal Catalyzed N- and C-Alkylation Reactions via Borrowing Hydrogen or Hydrogen Autotransfer

Torsten Irrgang et al.

CHEMICAL REVIEWS (2019)

Article Pharmacology & Pharmacy

Larotrectinib: First Global Approval

Lesley J. Scott

Review Chemistry, Multidisciplinary

Advances in One-Pot Synthesis through Borrowing Hydrogen Catalysis

Avelino Corma et al.

CHEMICAL REVIEWS (2018)

Article Chemistry, Multidisciplinary

Enantioselective Radical Cyclization for Construction of 5-Membered Ring Structures by Metalloradical C-H Alkylation

Yong Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Review Chemistry, Multidisciplinary

Key Green Chemistry research areas from a pharmaceutical manufacturers' perspective revisited

Marian C. Bryan et al.

GREEN CHEMISTRY (2018)

Article Chemistry, Multidisciplinary

Atropoenantioselective Redox-Neutral Amination of Biaryl Compounds through Borrowing Hydrogen and Dynamic Kinetic Resolution

Jianwei Zhang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Enantioselective amine α-functionalization via palladium-catalysed C-H arylation of thioamides

Pankaj Jain et al.

NATURE CHEMISTRY (2017)

Article Chemistry, Multidisciplinary

Nickel-Catalyzed N-Alkylation of Acylhydrazines and Arylamines Using Alcohols and Enantioselective Examples

Peng Yang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Pharmacology & Pharmacy

Glecaprevir/Pibrentasvir: First Global Approval

Yvette N. Lamb

Article Chemistry, Multidisciplinary

(Enantio) selective Hydrogen Autotransfer: Ruthenium-Catalyzed Synthesis of Oxazolidin-2-ones from Urea and Diols

Miguel Pena-Lopez et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Catalytic enantioselective OFF <-> ON activation processes initiated by hydrogen transfer: concepts and challenges

Adrien Quintard et al.

CHEMICAL COMMUNICATIONS (2016)

Article Chemistry, Organic

Two Scalable Syntheses of (S)-2-Methylazetidine

Matthew S. Dowling et al.

JOURNAL OF ORGANIC CHEMISTRY (2016)

Review Chemistry, Multidisciplinary

Transition-Metal-Catalyzed Hydrogen-Transfer Annulations: Access to Heterocyclic Scaffolds

Avanashiappan Nandakumar et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Review Chemistry, Multidisciplinary

Substitution of alcohols by N-nucleophiles via transition metal-catalyzed dehydrogenation

Qin Yang et al.

CHEMICAL SOCIETY REVIEWS (2015)

Article Chemistry, Multidisciplinary

Dynamic Kinetic Asymmetric Amination of Alcohols: From A Mixture of Four Isomers to Diastereo- and Enantiopure α-Branched Amines

Zi-Qiang Rong et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Chemistry, Applied

A Survey of the Borrowing Hydrogen Approach to the Synthesis of some Pharmaceutically Relevant Intermediates

John Leonard et al.

ORGANIC PROCESS RESEARCH & DEVELOPMENT (2015)

Article Multidisciplinary Sciences

Conversion of alcohols to enantiopure amines through dual-enzyme hydrogen-borrowing cascades

Francesco G. Mutti et al.

SCIENCE (2015)

Review Chemistry, Multidisciplinary

Catalytic Enantioselective C-H Functionalization of Alcohols by Redox-Triggered Carbonyl Addition: Borrowing Hydrogen, Returning Carbon

John M. Ketcham et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Chemistry, Multidisciplinary

A Regio-and Stereoselective w-Transaminase/ Monoamine Oxidase Cascade for the Synthesis of Chiral 2,5-Disubstituted Pyrrolidines**

Elaine O'Reilly et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Chemistry, Multidisciplinary

Organocatalytic asymmetric synthesis of chiral nitrogenous heterocycles and natural products

Jie Yu et al.

PURE AND APPLIED CHEMISTRY (2014)

Article Chemistry, Organic

Recent advances in organocatalytic asymmetric synthesis of polysubstituted pyrrolidines

Man-Yi Han et al.

TETRAHEDRON LETTERS (2014)

Article Chemistry, Multidisciplinary

An Iron/Amine-Catalyzed Cascade Process for the Enantioselective Functionalization of Allylic Alcohols

Adrien Quintard et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Review Chemistry, Inorganic & Nuclear

Metal-complexes of optically active amino- and imino-based pyridine ligands in asymmetric catalysis

Giorgio Chelucci

COORDINATION CHEMISTRY REVIEWS (2013)

Article Chemistry, Applied

Iridium-Catalyzed Enantioselective Hydrogenation of Cyclic Imines

Mingxin Chang et al.

ADVANCED SYNTHESIS & CATALYSIS (2010)

Article Chemistry, Multidisciplinary

Iridium-Catalyzed Asymmetric Hydrogenation of Cyclic Enamines

Guo-Hua Hou et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

Article Chemistry, Multidisciplinary

Ruthenium-Catalyzed N-Alkylation of Amines and Sulfonamides Using Borrowing Hydrogen Methodology

M. Haniti S. A. Hamid et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

Article Chemistry, Organic

Enantioselective Syntheses of Both Enantiomers of Noranabasamine

Lei Miao et al.

ORGANIC LETTERS (2009)

Review Biochemistry & Molecular Biology

Advances in matrix metalloproteinase inhibitors based on pyrrolidine scaffold

Xian-Chao Cheng et al.

CURRENT MEDICINAL CHEMISTRY (2008)

Review Pharmacology & Pharmacy

Looking to the future for erectile dysfunction therapies

Konstantinos Hatzimouratidis et al.

Article Chemistry, Inorganic & Nuclear

Synthesis and reactivities of Cp*Ir amide and hydride complexes bearing C-N chelate ligands

Sachiko Arita et al.

ORGANOMETALLICS (2008)

Article Chemistry, Inorganic & Nuclear

Borrowing hydrogen in an indirect asymmetric Wittig reaction

Duncan J. Shermer et al.

TETRAHEDRON-ASYMMETRY (2007)

Review Chemistry, Multidisciplinary

Asymmetric enamine catalysis

Santanu Mukherjee et al.

CHEMICAL REVIEWS (2007)

Review Chemistry, Multidisciplinary

Iminium catalysis

Anniina Erkkila et al.

CHEMICAL REVIEWS (2007)

Article Chemistry, Multidisciplinary

Gold(I)-catalyzed enantioselective intramolecular hydroamination of allenes

Rebecca L. LaLonde et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

Article Chemistry, Multidisciplinary

Chiral neutral zirconium amidate complexes for the asymmetric hydroamination of alkenes

Mark C. Wood et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2007)

Article Chemistry, Multidisciplinary

Enantioselective, palladium-catalyzed α-arylation of N-Boc-pyrrolidine

KR Campos et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)