Allenes and Dienes as Chiral Allylmetal Pronucleophiles in Catalytic Enantioselective C=X Addition: Historical Perspective and State‐of‐The‐Art Survey

Enantioselective Iridium-Catalyzed Allylic Alkylation of Racemic Branched Alkyl-Substituted Allylic Acetates with Malonates

(2021) Tian-Yuan Zhang et al.   ORGANIC LETTERS

Enantioselective C2-Allylation of Benzimidazoles Using 1,3-Diene Pronucleophiles

(2021) James Levi Knippel et al.   ORGANIC LETTERS

Dual Palladium/Photoredox-Catalyzed Enantioselective and Regioselective Decarboxylative Hydroaminoalkylation of Allenes

(2021) Jun Zheng et al.   ACS Catalysis

Access to Chiral Diamine Derivatives through Stereoselective Cu-Catalyzed Reductive Coupling of Imines and Allenamides

(2021) Toolika Agrawal et al.   JOURNAL OF ORGANIC CHEMISTRY

CuH-Catalyzed Regio- and Enantioselective Hydrocarboxylation of Allenes: Toward Carboxylic Acids with Acyclic Quaternary Centers

(2021) Sheng Feng et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

From Hydrogenation to Transfer Hydrogenation to Hydrogen Auto-Transfer in Enantioselective Metal-Catalyzed Carbonyl Reductive Coupling: Past, Present, and Future

(2021) Catherine Gazolla Santana et al.   ACS Catalysis

Enantioselective Ruthenium-BINAP-Catalyzed Carbonyl Reductive Coupling of Alkoxyallenes: Convergent Construction of syn-sec,tert-Diols via (Z)-σ-Allylmetal Intermediates

(2021) Ming Xiang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Catalytic Reductive Aldol and Mannich Reactions of Enone, Acrylate, and Vinyl Heteroaromatic Pronucleophiles

(2020) Cole C. Meyer et al.   CHEMICAL REVIEWS

Highly Enantioselective Synthesis of Indazoles with a C3-Quaternary Chiral Center Using CuH Catalysis

(2020) Yuxuan Ye et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Copper‐Catalyzed Borylative Couplings with C−N Electrophiles

(2020) Fabien J. T. Talbot et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Copper-Catalyzed Hydroalumination of Allenes with Diisobutylaluminum Hydride: Synthesis of Allylic Ketones with α-Quaternary Centers via Tandem Allylation/Oppenauer Oxidation

(2020) Sangback Lee et al.   ORGANIC LETTERS

Copper-Catalyzed Borylative Difunctionalization of π-Systems

(2020) Andrew Whyte et al.   ACS Catalysis

Metal-Catalyzed Intermolecular Hydrofunctionalization of Allenes: Easy Access to Allylic Structures via the Selective Formation of C–N, C–C, and C–O Bonds

(2020) Rémi Blieck et al.   CHEMICAL REVIEWS

CuH-Catalyzed Enantioselective Ketone Allylation with 1,3-Dienes: Scope, Mechanism, and Applications

(2019) Chengxi Li et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Cyclometalated Iridium–PhanePhos Complexes Are Active Catalysts in Enantioselective Allene–Fluoral Reductive Coupling and Related Alcohol-Mediated Carbonyl Additions That Form Acyclic Quaternary Carbon Stereocenters

(2019) Leyah A. Schwartz et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Enantioselective Allylation Using Allene, a Petroleum Cracking Byproduct

(2019) Richard Y. Liu et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Regio- and Enantioselective Iridium-Catalyzed N-Allylation of Indoles and Related Azoles with Racemic Branched Alkyl-Substituted Allylic Acetates

(2019) Seung Wook Kim et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Copper-Catalyzed Asymmetric Reductive Allylation of Ketones with 1,3-Dienes

(2019) Bin Fu et al.   ORGANIC LETTERS

Feedstock Reagents in Metal-Catalyzed Carbonyl Reductive Coupling: Minimizing Preactivation for Efficiency in Target-Oriented Synthesis

(2019) Rosalie S. Doerksen et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Copper–Hydride-Catalyzed Enantioselective Processes with Allenyl Boronates. Mechanistic Nuances, Scope, and Utility in Target-Oriented Synthesis

(2019) Yu Sun et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Construction of All‐Carbon Chiral Quaternary Centers via Cu(I)‐Catalyzed Enantioselective Reductive Hydroxymethylation of 1, 1‐Disubstituted Allenes with CO2

(2019) Kuiling Ding et al.   CHEMISTRY-A EUROPEAN JOURNAL

Direct Conversion of Primary Alcohols to 1,2-Amino Alcohols: Enantioselective Iridium-Catalyzed Carbonyl Reductive Coupling of Phthalimido-Allene via Hydrogen Auto-Transfer

(2019) Kim Spielmann et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Development of a Strategy for Linear-Selective Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral γ-Hydroxyaldehyde Equivalents

(2019) Raphael K. Klake et al.   ORGANIC LETTERS

Inversion of Enantioselectivity in Allene Gas versus Allyl Acetate Reductive Aldehyde Allylation Guided by Metal-Centered Stereogenicity: An Experimental and Computational Study

(2019) Seung Wook Kim et al.   ACS Catalysis

Engaging Aldehydes in CuH-Catalyzed Reductive Coupling Reactions: Stereoselective Allylation with Unactivated 1,3-Diene Pronucleophiles

(2019) Chengxi Li et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Highly Selective and Catalytic Generation of Acyclic Quaternary Carbon Stereocenters via Functionalization of 1,3-Dienes with CO2

(2019) Xiao-Wang Chen et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Access to a Catalytically Generated Umpolung Reagent through the Use of Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral Vicinal Aminoalcohol Synthons

(2019) Samantha L. Gargaro et al.   ORGANIC LETTERS

Copper-Catalyzed Functionalization of 1,3-Dienes: Hydrofunctionalization, Borofunctionalization, and Difunctionalization

(2019) Gregory J. P. Perry et al.   ACS Catalysis

Intermolecular Metal-Catalyzed Reductive Coupling of Dienes, Allenes, and Enynes with Carbonyl Compounds and Imines

(2018) Michael Holmes et al.   CHEMICAL REVIEWS

Catalytic nucleophilic ‘umpoled’ π-allyl reagents

(2018) Kim Spielmann et al.   CHEMICAL SOCIETY REVIEWS

A Regio- and Enantioselective CuH-Catalyzed Ketone Allylation with Terminal Allenes

(2018) Erica Y. Tsai et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Amphiphilic π-Allyliridium C,O-Benzoates Enable Regio- and Enantioselective Amination of Branched Allylic Acetates Bearing Linear Alkyl Groups

(2018) Arismel Tena Meza et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Recent advances on catalytic asymmetric difunctionalization of 1,3-dienes

(2018) Yang Xiong et al.   TETRAHEDRON LETTERS

Catalytic Enantioselective Carbonyl Propargylation Beyond Preformed Carbanions: Reductive Coupling and Hydrogen Auto-Transfer

(2018) Brett R. Ambler et al.   ChemCatChem

Iridium-Catalyzed Asymmetric Allylic Substitution Reactions

(2018) Qiang Cheng et al.   CHEMICAL REVIEWS

Regio- and Enantioselective Iridium-Catalyzed Amination of Racemic Branched Alkyl-Substituted Allylic Acetates with Primary and Secondary Aromatic and Heteroaromatic Amines

(2018) Seung Wook Kim et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Cu-Catalyzed Enantioselective Reductive Coupling of 1,3-Dienes and Aldimines

(2018) Mingfeng Li et al.   ORGANIC LETTERS

Stereochemical Characterization of Polyketide Stereotriads Synthesized via Hydrogen-Mediated Asymmetric syn-Crotylation

(2017) Mathilde Pantin et al.   JOURNAL OF ORGANIC CHEMISTRY

Enantioselective Formation of CF3-Bearing All-Carbon Quaternary Stereocenters via C–H Functionalization of Methanol: Iridium Catalyzed Allene Hydrohydroxymethylation

(2017) Michael Holmes et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Highly Regio- and Enantioselective Copper-Catalyzed Reductive Hydroxymethylation of Styrenes and 1,3-Dienes with CO2

(2017) Yong-Yuan Gui et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Enantioselective copper catalysed, direct functionalisation of allenes via allyl copper intermediates

(2017) Alexander P. Pulis et al.   Chemical Science

Regiodivergent and Diastereoselective CuH-Catalyzed Allylation of Imines with Terminal Allenes

(2016) Richard Y. Liu et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Enantioselective Formation of All-Carbon Quaternary Centers via C–H Functionalization of Methanol: Iridium-Catalyzed Diene Hydrohydroxymethylation

(2016) Khoa D. Nguyen et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Metal-catalyzed reductive coupling of olefin-derived nucleophiles: Reinventing carbonyl addition

(2016) Khoa D. Nguyen et al.   SCIENCE

Recent Advances in the Asymmetric Nozaki–Hiyama–Kishi Reaction

(2016) Guozhu Zhang et al.   SYNTHESIS-STUTTGART

Diene hydroaminomethylation via ruthenium-catalyzed C–C bond forming transfer hydrogenation: beyond carbonylation

(2016) Susumu Oda et al.   Chemical Science

Hydroaminomethylation Beyond Carbonylation: Allene-Imine Reductive Coupling by Ruthenium-Catalyzed Transfer Hydrogenation

(2015) Susumu Oda et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Ruthenium-Catalyzed CC Coupling of Fluorinated Alcohols with Allenes: Dehydrogenation at the Energetic Limit of β-Hydride Elimination

(2015) Brannon Sam et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Ruthenium-Catalyzed Asymmetric Hydrohydroxyalkylation of Butadiene: The Role of the Formyl Hydrogen Bond in Stereochemical Control

(2015) Matthew N. Grayson et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Copper-catalyzed borylative transformations of non-polar carbon–carbon unsaturated compounds employing borylcopper as an active catalyst species

(2015) Kazuhiko Semba et al.   TETRAHEDRON

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

(2014) John M. Ketcham et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Paraformaldehyde and Methanol as C1 Feedstocks in Metal-Catalyzed CC Couplings of π-Unsaturated Reactants: Beyond Hydroformylation

(2014) Brannon Sam et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Catalytic asymmetric allylation of carbonyl compounds and imines with allylic boronates

(2014) Hua-Xing Huo et al.   Organic Chemistry Frontiers

Ruthenium Catalyzed Reductive Coupling of Paraformaldehyde to Trifluoromethyl Allenes: CF3-Bearing All-Carbon Quaternary Centers

(2013) Brannon Sam et al.   ORGANIC LETTERS

Regiodivergent reductive coupling of 2-substituted dienes to formaldehyde employing ruthenium or nickel catalyst: hydrohydroxymethylation via transfer hydrogenation

(2013) Alexander Köpfer et al.   Chemical Science

Chiral-Anion-Dependent Inversion of Diastereo- and Enantioselectivity in Carbonyl Crotylation via Ruthenium-Catalyzed Butadiene Hydrohydroxyalkylation

(2012) Emma L. McInturff et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Enantioselective Copper-Catalyzed Reductive Coupling of Alkenylazaarenes with Ketones

(2012) Aakarsh Saxena et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Enantioselective C-H Crotylation of Primary Alcohols via Hydrohydroxyalkylation of Butadiene

(2012) J. R. Zbieg et al.   SCIENCE

Catalytic Enantioselective Allylation of Carbonyl Compounds and Imines

(2011) Miguel Yus et al.   CHEMICAL REVIEWS

Diastereo- and Enantioselective Ruthenium-Catalyzed Hydrohydroxyalkylation of 2-Silyl-butadienes: Carbonylsyn-Crotylation from the Alcohol Oxidation Level

(2011) Jason R. Zbieg et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Iridium-catalysed direct C–C coupling of methanol and allenes

(2011) Joseph Moran et al.   Nature Chemistry

cis-2,5-Diaminobicyclo[2.2.2]octane, a New Scaffold for Asymmetric Catalysis via Salen−Metal Complexes

(2011) James D. White et al.   ORGANIC LETTERS

Efficient One-to-One Coupling of Easily Available 1,3-Dienes with Carbon Dioxide

(2011) Jun Takaya et al.   ORGANIC LETTERS

Iridium-Catalyzed Hydrohydroxyalkylation of Butadiene: Carbonyl Crotylation

(2010) Jason R. Zbieg et al.   ADVANCED SYNTHESIS & CATALYSIS

Enantioselective Carbonyl Allylation, Crotylation, andtert-Prenylation of Furan Methanols and Furfurals via Iridium-Catalyzed Transfer Hydrogenation

(2010) Benjamin Bechem et al.   JOURNAL OF ORGANIC CHEMISTRY

Chiral Brønsted Acid-Catalyzed Allylboration of Aldehydes

(2010) Pankaj Jain et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Amplification of Anti-Diastereoselectivity via Curtin−Hammett Effects in Ruthenium-Catalyzed Hydrohydroxyalkylation of 1,1-Disubstituted Allenes: Diastereoselective Formation of All-Carbon Quaternary Centers

(2010) Jason R. Zbieg et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Allenamide Hydro−Hydroxyalkylation: 1,2-Amino Alcohols via Ruthenium-Catalyzed Carbonylanti-Aminoallylation

(2010) Jason R. Zbieg et al.   ORGANIC LETTERS

Enantioselective Allylation, Crotylation, and Reverse Prenylation of Substituted Isatins: Iridium-Catalyzed CC Bond-Forming Transfer Hydrogenation

(2009) Junji Itoh et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

anti-Aminoallylation of Aldehydes via Ruthenium-Catalyzed Transfer Hydrogenative Coupling of Sulfonamido Allenes: 1,2-Aminoalcohols

(2009) Eduardas Skucas et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Enantioselective Carbonyl Reverse Prenylation from the Alcohol or Aldehyde Oxidation Level Employing 1,1-Dimethylallene as the Prenyl Donor

(2009) Soo Bong Han et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

anti-Diastereo- and Enantioselective Carbonyl Crotylation from the Alcohol or Aldehyde Oxidation Level Employing a Cyclometallated Iridium Catalyst: α-Methyl Allyl Acetate as a Surrogate to Preformed Crotylmetal Reagents

(2009) In Su Kim et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

All-Carbon Quaternary Centers via Ruthenium-Catalyzed Hydroxymethylation of 2-Substituted Butadienes Mediated by Formaldehyde: Beyond Hydroformylation

(2009) Tomas Smejkal et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Rh-Catalyzed Reductive Coupling Reaction of Aldehydes with Conjugated Dienes Promoted by Triethylborane

(2009) Masanari Kimura et al.   ORGANIC LETTERS

Catalytic Carbonyl Addition through Transfer Hydrogenation: A Departure from Preformed Organometallic Reagents

(2008) John F. Bower et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Enantioselective Iridium-Catalyzed Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level Using Allyl Acetate as an Allyl Metal Surrogate

(2008) In Su Kim et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Enantioselective Iridium-Catalyzed Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level via Transfer Hydrogenative Coupling of Allyl Acetate: Departure from Chirally Modified Allyl Metal Reagents in Carbonyl Addition

(2008) In Su Kim et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Ruthenium-Catalyzed C−C Bond Forming Transfer Hydrogenation: Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level Employing Acyclic 1,3-Dienes as Surrogates to Preformed Allyl Metal Reagents

(2008) Fumitoshi Shibahara et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Hydrocarboxylation of Allenes with CO2Catalyzed by Silyl Pincer-Type Palladium Complex

(2008) Jun Takaya et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Further Improvement on Sulfonamide-Based Ligand for Catalytic Asymmetric 2-Haloallylation and Allylation

(2008) Zhiyu Zhang et al.   ORGANIC LETTERS

Ruthenium Catalyzed C−C Bond Formation via Transfer Hydrogenation: Branch-Selective Reductive Coupling of Allenes to Paraformaldehyde and Higher Aldehydes

(2008) Ming-Yu Ngai et al.   ORGANIC LETTERS

Iridium-Catalyzed C−C Coupling via Transfer Hydrogenation:  Carbonyl Addition from the Alcohol or Aldehyde Oxidation Level Employing 1,3-Cyclohexadiene

(2008) John F. Bower et al.   ORGANIC LETTERS

Synthesis of non-symmetric bis(oxazoline)-containing ligands and their application in the catalytic enantioselective Nozaki–Hiyama–Kishi allylation of benzaldehyde

(2007) Gráinne C. Hargaden et al.   ORGANIC & BIOMOLECULAR CHEMISTRY