Search results for: Armando Córdova

Items from 1 to 20 out of 87 results

article

Sugar‐Assisted Kinetic Resolutions in Metal/Chiral Amine Co‐Catalyzed α‐Allylations and [4+2] Cycloadditions: Highly Enantioselective Synthesis of Sugar and Chromane Derivatives

Kaiheng Zhang, Chrislaura Carmo, Luca Deiana, Erik Svensson Grape, more

Chemistry – A European Journal > 29 > 53 > n/a - n/a

Functionalized triose‐, furanose and chromane‐derivatives were synthesized by the titled reactions. The sugar‐assisted kinetic resolution/C−C bond‐forming cascade processes generate a functionalized sugar derivative with a quaternary stereocenter in a highly enantioselective fashion (up to >99 % ee) by using a simple combination of metal and chiral amine co‐catalysts. Notably, the interplay between...

article

Regio‐ and Stereoselective Carbon‐Boron Bond Formation via Heterogeneous Palladium‐Catalyzed Hydroboration of Enallenes

Veluru Ramesh Naidu, Abdolrahim A. Rafi, Cheuk‐Wai Tai, Jan‐E. Bäckvall, more

Chemistry – A European Journal > 29 > 24 > n/a - n/a

A highly efficient regio‐ and stereoselective heterogeneous palladium‐catalyzed hydroboration reaction of enallenes was developed. Nanopalladium immobilized on microcrystalline cellulose (MCC) was successfully employed as an efficient catalyst for the enallene hydroboration reaction. The nanopalladium particles were shown by HAADF‐STEM to have an average size of 2.4 nm. The cellulose‐supported palladium...

article

Off‐Cycle Catalyst Cooperativity in Amine/Transition Metal Combined Catalysis: Bicyclo[3.2.0]heptanes as Key Species in Co‐Catalytic Enantioselective Carbocyclizations

Samson Afewerki, Guangning Ma, Luca Deiana, Hongli Wu, more

Advanced Synthesis & Catalysis > 364 > 8 > 1394 - 1401

The existence of off‐cycle catalyst cooperativity in amine/metal combined catalysis is disclosed. The experimental and density functional theory study of the amine/metal co‐catalyzed enantioselective Michael/carbocyclization cascade reaction between allenes and α,β‐unsaturated aldehydes reveals that the dual catalysts can perform off‐cycle cooperativity that gives access to stable bicyclo[3.2.0]heptane...

article

Solvent Dependency in Stereoselective δ‐Lactam Formation of Chiral α‐Fluoromalonate Derivatives: Stereodivergent Synthesis of Heterocycles with Fluorine Containing Stereocenters Adjacent to Tertiary Stereocenters

Kaiheng Zhang, Xiang Sheng, Luca Deiana, Erik Svensson Grape, more

Advanced Synthesis & Catalysis > 364 > 5 > 958 - 965

The discovery and investigation of solvent dependency in stereoselective intramolecular amidation of chiral 5‐aminofunctionalized‐2‐fluoromalonate ester derivatives, which gives access to highly functionalized δ‐lactams with a quaternary fluorine‐containing stereocenter, is disclosed. Experimental work together with density functional theory calculations led to understanding of how to direct and switch...

article

Accelerating Amine‐Catalyzed Asymmetric Reactions by Intermolecular Cooperative Thiourea/Oxime Hydrogen‐Bond Catalysis

Guangning Ma, Samson Afewerki, Kaiheng Zhang, Ismail Ibrahem, more

European Journal of Organic Chemistry > 2021 > 21 > 3043 - 3049

The ability of intermolecular cooperative thiourea/oxime hydrogen‐bond catalysis for improving and accelerating asymmetric aminocatalysis is presented. The two readily available hydrogen‐bond‐donating catalysts operates in synergy with a chiral amine catalyst to accomplish highly stereoselective transformations. The synergistic catalyst systems simultaneously activate both electrophiles and nucleophiles,...

article

Silver‐Triggered Activity of a Heterogeneous Palladium Catalyst in Oxidative Carbonylation Reactions

Man‐Bo Li, Ying Yang, Abdolrahim A. Rafi, Michael Oschmann, more

Angewandte Chemie International Edition > 59 > 26 > 10391 - 10395

A silver‐triggered heterogeneous Pd‐catalyzed oxidative carbonylation has been developed. This heterogeneous process exhibits high efficiency and good recyclability, and was utilized for the one‐pot construction of polycyclic compounds with multiple chiral centers. AgOTf was used to remove chloride ions in the heterogeneous catalyst Pd‐AmP‐CNC, thereby generating highly active Pd^II, which results...

article

Silver‐Triggered Activity of a Heterogeneous Palladium Catalyst in Oxidative Carbonylation Reactions

Man‐Bo Li, Ying Yang, Abdolrahim A. Rafi, Michael Oschmann, more

Angewandte Chemie > 132 > 26 > 10477 - 10481

article

Enamine/Transition Metal Combined Catalysis: Catalytic Transformations Involving Organometallic Electrophilic Intermediates

Samson Afewerki, Armando Córdova

Topics in Current Chemistry > 2019 > 377 > 6 > 1-27

The concept of merging enamine activation catalysis with transition metal catalysis is an important strategy, which allows for selective chemical transformations not accessible without this combination. The amine catalyst activates the carbonyl compounds through the formation of a reactive nucleophilic enamine intermediate and, in parallel, the transition metal activates a wide range of functionalities...

article

Total Asymmetric Synthesis of Quinine, Quinidine, and Analogues via Catalytic Enantioselective Cascade Transformations

Yan Jiang, Luca Deiana, Kaiheng Zhang, Shuangzheng Lin, more

European Journal of Organic Chemistry > 2019 > 35 > 6016 - 6023

A catalytic asymmetric strategy for the total synthesis of quinuclidine natural products, which includes the completed enantioselective synthesis of the classical targets quinine and quinidine is disclosed. It is based on catalytic asymmetric cascade transformations, which paves the road for the synthesis of both enantiomers of the crucial C4 stereocenter with high enantioselectivity (up to 99 % ee...

article

Front Cover: Total Asymmetric Synthesis of Quinine, Quinidine, and Analogues via Catalytic Enantioselective Cascade Transformations (Eur. J. Org. Chem. 35/2019)

Yan Jiang, Luca Deiana, Kaiheng Zhang, Shuangzheng Lin, more

European Journal of Organic Chemistry > 2019 > 35 > 6003 - 6003

The Front Cover shows a versatile catalytic asymmetric strategy for the total synthesis of quinuclidine natural products, which includes the completed enantioselective synthesis of the classical targets quinine and quinidine More information can be found in the Communication by A. Córdova et al.

article

Cover Feature: Catalytic Enantioselective Synthesis of Bicyclic Lactam N,S‐Acetals in One Pot by Cascade Transformations (Eur. J. Org. Chem. 29/2019)

Kaiheng Zhang, Luca Deiana, Erik Svensson Grape, A. Ken Inge, more

European Journal of Organic Chemistry > 2019 > 29 > 4625 - 4625

The Cover Feature shows a versatile strategy for the enantioselective synthesis of bicyclic lactam N,S‐acetals by one‐pot cascade transformations. The transformations between readily available substrates is promoted by chiral amines and creates bicyclic or tricyclic lactam N,S‐acetals with high chemo‐ and stereoselectivity (up to >99.5:0.5 d.r. and >99% ee) in one‐pot operations More information...

article

Catalytic Enantioselective Synthesis of Bicyclic Lactam N,S‐Acetals in One Pot by Cascade Transformations

Kaiheng Zhang, Luca Deiana, Erik Svensson Grape, A. Ken Inge, more

European Journal of Organic Chemistry > 2019 > 29 > 4649 - 4657

A versatile strategy for the enantioselective synthesis of bicyclic lactam N,S‐acetals by one‐pot cascade transformations is disclosed. The transformation of readily available substrates is promoted by chiral amines and creates bicyclic or tricyclic lactam N,S‐acetals with high chemo‐ and stereoselectivity (up to > 99.5:0.5 dr and > 99 % ee) in one‐pot operations.

article

Highly Diastereo‐ and Enantioselective Cascade Synthesis of Bicyclic Lactams in One‐Pot

Yan Jiang, Luca Deiana, Rana Alimohammadzadeh, Leifeng Liu, more

European Journal of Organic Chemistry > 2018 > 9 > 1158 - 1164

A versatile and highly stereoselective synthetic route to functionalized bi‐ and tricyclic lactams (up to > 20:1 dr and 99 % ee) in one pot from simple starting materials (allylic alcohols, enals, diamines and amino alcohols) using cascade transformations promoted by chiral amine/Brønsted or metal/chiral amine/Brønsted relay catalysis is disclosed. Here molecular oxygen is employed as the terminal...

article

Selective Access to All Four Diastereomers of a 1,3‐Amino Alcohol by Combination of a Keto Reductase‐ and an Amine Transaminase‐Catalysed Reaction

Hannes Kohls, Mattias Anderson, Jonathan Dickerhoff, Klaus Weisz, more

Advanced Synthesis & Catalysis > 357 > 8 > 1808 - 1814

The biocatalytic synthesis of chiral amines has become a valuable addition to the chemists’ toolbox. However, the efficient asymmetric synthesis of functionalised amines bearing more than one stereocentre, such as 1,3‐amino alcohols, remains challenging. By employing a keto reductase (KRED) and two enantiocomplementary amine transaminases (ATA), we developed a biocatalytic route towards all four diastereomers...

article

Combined Heterogeneous Metal/Chiral Amine: Multiple Relay Catalysis for Versatile Eco‐Friendly Synthesis

Luca Deiana, Yan Jiang, Carlos Palo‐Nieto, Samson Afewerki, more

Angewandte Chemie > 126 > 13 > 3515 - 3519

Herein is described a versatile and broad synergistic strategy for expansion of chemical space and the synthesis of valuable molecules (e.g. carbocycles and heterocycles), with up to three quaternary stereocenters, in a highly enantioselective fashion from simple alcohols (31 examples, 95:5 to >99.5:0.5 e.r.) using integrated heterogeneous metal/chiral amine multiple relay catalysis and air/O₂...

article

Combined Heterogeneous Metal/Chiral Amine: Multiple Relay Catalysis for Versatile Eco‐Friendly Synthesis

Luca Deiana, Yan Jiang, Carlos Palo‐Nieto, Samson Afewerki, more

Angewandte Chemie International Edition > 53 > 13 > 3447 - 3451

article

A Palladium/Chiral Amine Co‐catalyzed Enantioselective Dynamic Cascade Reaction: Synthesis of Polysubstituted Carbocycles with a Quaternary Carbon Stereocenter

Guangning Ma, Samson Afewerki, Luca Deiana, Carlos Palo‐Nieto, more

Angewandte Chemie > 125 > 23 > 6166 - 6170

Polysubstituierte fünf‐ und sechsgliedrige Carbocyclen wurden mit der Titelreaktion erhalten. Der dynamische Eintopf‐Staffelprozess erzeugt mit einer einfachen Katalysatorkombination aus Palladium und einem chiralen Amin hoch enantioselektiv (99.5:0.5→99:0.5 e.r.) vier neue Stereozentren, darunter ein quartäres Kohlenstoffzentrum.

article

A Palladium/Chiral Amine Co‐catalyzed Enantioselective Dynamic Cascade Reaction: Synthesis of Polysubstituted Carbocycles with a Quaternary Carbon Stereocenter

Guangning Ma, Samson Afewerki, Luca Deiana, Carlos Palo‐Nieto, more

Angewandte Chemie International Edition > 52 > 23 > 6050 - 6054

Polysubstituted 5‐ and 6‐membered carbocycles were synthesized by the title reaction. The one‐pot dynamic relay process generates four new stereocenters, including a quaternary carbon center, in a highly enantioselective fashion (99.5:0.5→99:0.5 e.r.) by using a simple combination of palladium and chiral amine co‐catalysts.

article

Palladium/Chiral Amine Co‐catalyzed Enantioselective β‐Arylation of α,β‐Unsaturated Aldehydes

Ismail Ibrahem, Guangning Ma, Samson Afewerki, Armando Córdova

Angewandte Chemie > 125 > 3 > 912 - 916

Eine Kombination aus Palladium und einem einfachen chiralen Amin als Cokatalysatoren wird für die enantioselektive konjugierte Addition von Arylboronsäuren an α,β‐ungesättigte Aldehyde genutzt (siehe Schema). Den präparativen Nutzen dieser cokatalysierten Reaktion belegen die kurzen Totalsynthesen von (R)‐(−)‐Curcumen and 4‐Aryl‐2‐onen.

article

Palladium/Chiral Amine Co‐catalyzed Enantioselective β‐Arylation of α,β‐Unsaturated Aldehydes

Ismail Ibrahem, Guangning Ma, Samson Afewerki, Armando Córdova

Angewandte Chemie International Edition > 52 > 3 > 878 - 882

Palladium and a simple chiral amine are used as co‐catalysts for the enantioselective conjugate addition of aryl boronic acids to α,β‐unsaturated aldehydes (see scheme). The synthetic utility of this co‐catalyzed reaction was demonstrated in the short total syntheses of (R)‐(−)‐curcumene and 4‐aryl‐2‐ones.

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ASYMMETRIC CATALYSIS (16)
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Search results for: Armando Córdova

Sugar‐Assisted Kinetic Resolutions in Metal/Chiral Amine Co‐Catalyzed α‐Allylations and [4+2] Cycloadditions: Highly Enantioselective Synthesis of Sugar and Chromane Derivatives

Regio‐ and Stereoselective Carbon‐Boron Bond Formation via Heterogeneous Palladium‐Catalyzed Hydroboration of Enallenes

Off‐Cycle Catalyst Cooperativity in Amine/Transition Metal Combined Catalysis: Bicyclo[3.2.0]heptanes as Key Species in Co‐Catalytic Enantioselective Carbocyclizations

Solvent Dependency in Stereoselective δ‐Lactam Formation of Chiral α‐Fluoromalonate Derivatives: Stereodivergent Synthesis of Heterocycles with Fluorine Containing Stereocenters Adjacent to Tertiary Stereocenters

Accelerating Amine‐Catalyzed Asymmetric Reactions by Intermolecular Cooperative Thiourea/Oxime Hydrogen‐Bond Catalysis

Silver‐Triggered Activity of a Heterogeneous Palladium Catalyst in Oxidative Carbonylation Reactions

Silver‐Triggered Activity of a Heterogeneous Palladium Catalyst in Oxidative Carbonylation Reactions

Enamine/Transition Metal Combined Catalysis: Catalytic Transformations Involving Organometallic Electrophilic Intermediates

Total Asymmetric Synthesis of Quinine, Quinidine, and Analogues via Catalytic Enantioselective Cascade Transformations

Front Cover: Total Asymmetric Synthesis of Quinine, Quinidine, and Analogues via Catalytic Enantioselective Cascade Transformations (Eur. J. Org. Chem. 35/2019)

Cover Feature: Catalytic Enantioselective Synthesis of Bicyclic Lactam N,S‐Acetals in One Pot by Cascade Transformations (Eur. J. Org. Chem. 29/2019)

Catalytic Enantioselective Synthesis of Bicyclic Lactam N,S‐Acetals in One Pot by Cascade Transformations

Highly Diastereo‐ and Enantioselective Cascade Synthesis of Bicyclic Lactams in One‐Pot

Selective Access to All Four Diastereomers of a 1,3‐Amino Alcohol by Combination of a Keto Reductase‐ and an Amine Transaminase‐Catalysed Reaction

Combined Heterogeneous Metal/Chiral Amine: Multiple Relay Catalysis for Versatile Eco‐Friendly Synthesis

Combined Heterogeneous Metal/Chiral Amine: Multiple Relay Catalysis for Versatile Eco‐Friendly Synthesis

A Palladium/Chiral Amine Co‐catalyzed Enantioselective Dynamic Cascade Reaction: Synthesis of Polysubstituted Carbocycles with a Quaternary Carbon Stereocenter

A Palladium/Chiral Amine Co‐catalyzed Enantioselective Dynamic Cascade Reaction: Synthesis of Polysubstituted Carbocycles with a Quaternary Carbon Stereocenter

Palladium/Chiral Amine Co‐catalyzed Enantioselective β‐Arylation of α,β‐Unsaturated Aldehydes

Palladium/Chiral Amine Co‐catalyzed Enantioselective β‐Arylation of α,β‐Unsaturated Aldehydes

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