4.7 Article

Hydrogen-Bond-Donor-Directed Switching of Enantioselectivity in the Vinylogous Aldol-Cyclization Cascade Reaction of Prostereogenic 3-Alkylidene Oxindoles with Isatins and o-Quinones

Related references

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

Catalytic Asymmetric Dearomative 1,3-Dipolar Cycloaddition of 2-Nitrobenzothiophenes and Isatin-Derived Azomethine Ylides

Jian-Qiang Zhao et al.

Summary: An enantioselective dearomative 1,3-dipolar cyclo-addition of 2-nitrobenzothiophenes and isatin-derived azomethine ylides was achieved using a bifunctional hydrogen-bonding thiourea catalyst, resulting in excellent yields and enantioselectivity. The chiral selectivity could be reversed by a bifunctional hydrogen-bonding squaramide catalyst with the same chiral source. DFT calculations provided insights into the stereochemistry and enantioselectivity reversal observed in the reaction.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

Enantioselective organocatalytic vinylogous aldol-cyclization cascade reaction of 3-alkylidene oxindoles with o-quinones

Yun-Jie Tsou et al.

Summary: The spirocyclic o-quinone analogues have shown a wide range of applications as biologically active compounds. A novel chiral bifunctional squaramide catalyst was used to catalyze the asymmetric vinylogous aldol-cyclization cascade reaction, resulting in the synthesis of enantioenriched spirocyclic o-quinone analogues with quaternary stereocenters in high yields and high enantioselectivities.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

Article Chemistry, Applied

Solvent-Dependent Enantiodivergent Friedel-Crafts Reaction of Arylsulfonyl Indoles with 1-Naphthols

Chia-Hao Chang et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

Article Chemistry, Multidisciplinary

Stereodivergent Construction of Tertiary Fluorides in Vicinal Stereogenic Pairs by Allylic Substitution with Iridium and Copper Catalysts

Zhi-Tao He et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Multidisciplinary Sciences

Enantiodivergence by minimal modification of an acyclic chiral secondary aminocatalyst

Jun Dai et al.

NATURE COMMUNICATIONS (2019)

Article Chemistry, Multidisciplinary

Direct Catalytic Asymmetric Aldol Reaction of α-Alkoxyamides to α-Fluorinated Ketones

Roman Pluta et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Copper(I)-Catalyzed Enantio- and Diastereodivergent Borylative Coupling of Styrenes and Imines

Taisuke Itoh et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Stereodivergent Synthesis of Tetrahydrofuroindoles through Pd-Catalyzed Asymmetric Dearomative Formal [3+2] Cycloaddition

Qiang Cheng et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Review Chemistry, Multidisciplinary

Stereodivergent Catalysis

Irina P. Beletskaya et al.

CHEMICAL REVIEWS (2018)

Article Chemistry, Multidisciplinary

Stereodivergent Synthesis of α,α-Disubstituted α-Amino Acids via Synergistic Cu/Ir Catalysis

Liang Wei et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Chemistry, Multidisciplinary

Ir/Cu Dual Catalysis: Enantio- and Diastereodivergent Access to alpha,alpha-Disubstituted alpha-Amino Acids Bearing Vicinal Stereocenters

Xiaohong Huo et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Chemistry, Multidisciplinary

Stereodivergent Allylic Substitutions with Aryl Acetic Acid Esters by Synergistic Iridium and Lewis Base Catalysis

Xingyu Jiang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Chemistry, Multidisciplinary

Stereodivergent Coupling of Aldehydes and Alkynes via Synergistic Catalysis Using Rh and Jacobsen's Amine

Faben A. Cruz et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Chemistry, Multidisciplinary

Diastereodivergent Asymmetric Carboamination/Annulation of Cyclopropenes with Aminoalkenes by Chiral Lanthanum Catalysts

Huai-Long Teng et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Review Chemistry, Multidisciplinary

Stereodivergence in Asymmetric Catalysis

Simon Krautwald et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Chemistry, Physical

Chiral Switchable Catalysts for Dynamic Control of Enantioselectivity

Giuseppe Romanazzi et al.

ACS CATALYSIS (2017)

Article Chemistry, Multidisciplinary

Catalyst-Controlled, Enantioselective, and Diastereodivergent Conjugate Addition of Aldehydes to Electron-Deficient Olefins

S. B. Jennifer Kan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Review Chemistry, Multidisciplinary

Switchable divergent asymmetric synthesis via organocatalysis

Gu Zhan et al.

CHEMICAL SOCIETY REVIEWS (2017)

Article Chemistry, Multidisciplinary

Diastereodivergent Construction of Bicyclic γ-Lactones via Enantioselective Ketone Hydroacylation

Xuesong Wu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

An Ir/Zn Dual Catalysis for Enantio- and Diastereodivergent α-Allylation of α-Hydroxyketones

Xiaohong Huo et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

Cinchona Urea-Catalyzed Asymmetric Sulfa-Michael Reactions: The Bronsted Acid-Hydrogen Bonding Model

Matthew N. Grayson et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

Temperature-Controlled Bidirectional Enantioselectivity in a Dynamic Catalyst for Asymmetric Hydrogenation

Golo Storch et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Organic

Vinylogous Reactivity of Oxindoles Bearing Nonsymmetric 3-Alkylidene Groups

Nicola Di Iorio et al.

JOURNAL OF ORGANIC CHEMISTRY (2015)

Article Multidisciplinary Sciences

Diastereodivergent organocatalytic asymmetric vinylogous Michael reactions

Xin Li et al.

NATURE COMMUNICATIONS (2014)

Article Chemistry, Multidisciplinary

Switchable Diastereoselectivity in Enantioselective [4+2] Cycloadditions with Simple Olefins by Asymmetric Binary Acid Catalysis

Jian Lv et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Article Chemistry, Multidisciplinary

Enantioselective Cyanoethoxycarbonylation of Isatins Promoted by a Lewis Base-Bronsted Acid Cooperative Catalyst

Yoshihiro Ogura et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Review Chemistry, Multidisciplinary

New advances in dual stereocontrol for asymmetric reactions

Jorge Escorihuela et al.

CHEMICAL SOCIETY REVIEWS (2013)

Article Chemistry, Multidisciplinary

Solvent-Dependent Enantiodivergence in the Chlorocyclization of Unsaturated Carbamates

Atefeh Garzan et al.

CHEMISTRY-A EUROPEAN JOURNAL (2013)

Article Chemistry, Multidisciplinary

Enantiodivergent and gamma-Selective Asymmetric Allylic Amination

Jianmin Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

Review Chemistry, Multidisciplinary

Isatins As Privileged Molecules in Design and Synthesis of Spiro-Fused Cyclic Frameworks

Girija S. Singh et al.

CHEMICAL REVIEWS (2012)

Article Chemistry, Multidisciplinary

Catalytic Asymmetric Diastereodivergent Deracemization

Marco Luparia et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

Article Chemistry, Applied

Enantioselective Aza-Morita-Baylis-Hillman Reaction Using Aliphatic alpha-Amidosulfones as Imine Surrogates

Nacim Abermil et al.

ADVANCED SYNTHESIS & CATALYSIS (2010)

Article Chemistry, Multidisciplinary

Solvent-Dependent Enantiodivergent Mannich-Type Reaction: Utilizing a Conformationally Flexible Guanidine/Bisthiourea Organocatalyst

Yoshihiro Sohtome et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2010)

Article Chemistry, Multidisciplinary

Mechanism of Amido-Thiourea Catalyzed Enantioselective Imine Hydrocyanation: Transition State Stabilization via Multiple Non-Covalent Interactions

Stephan J. Zuend et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

Article Chemistry, Multidisciplinary

Linking Structural Dynamics and Functional Diversity in Asymmetric Catalysis

Akihiro Nojiri et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

Article Chemistry, Multidisciplinary

Highly Diastereoselective Switchable Enantioselective Mannich Reaction of Glycine Derivatives with Imines

Xiao-Xia Yan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

Review Chemistry, Organic

New Approach for Complete Reversal of Enantioselectivity Using a Single Chiral Source

Takanori Tanaka et al.

SYNTHESIS-STUTTGART (2008)

Review Chemistry, Multidisciplinary

Cooperative catalysis by tertiary amino-thioureas: Mechanism and basis for enantioselectivity of ketone cyanosilylation

Stephan J. Zuend et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

Article Chemistry, Multidisciplinary

Theoretical studies on the bifunctionality of chiral thiourea-based organocatalysts:: Competing routes to C-C bond formation

Andrea Hamza et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

Article Chemistry, Multidisciplinary

Enantio- and diastereoselective Michael reaction of 1,3-dicarbonyl compounds to nitroolefins catalyzed by a bifunctional thiourea

T Okino et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2005)