4.8 Article

Enantioselective Desymmetrization of 3-Substituted Oxetanes: An Efficient Access to Chiral 3,4-Dihydro-2H-1,4-benzoxazines

Related references

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

Mild C-C Bond Formation via Lewis Acid Catalyzed Oxetane Ring Opening with Soft Carbon Nucleophiles

Hai Huang et al.

Summary: The use of soft carbon nucleophiles to open oxetanes has been developed for efficient C-C bond formation. Silyl ketene acetals and styrene-based carbon nucleophiles can generate a wide range of highly oxygenated molecules in the presence of catalysts, which are key substructures in natural products.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Review Chemistry, Multidisciplinary

Recent Advances in Enantioselective Desymmetrizations of Prochiral Oxetanes

Alexander Sandvoss et al.

Summary: Strain relief of oxetanes provides numerous opportunities for synthesizing chiral alcohols and ethers. Enantioselective desymmetrization serves as a powerful tool for constructing molecular complexity through transition metal, Lewis acid, and Bronsted acid catalysis, showcasing the immense possibilities for synthetic application.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Article Chemistry, Multidisciplinary

Asymmetric Pnictogen-Bonding Catalysis: Transfer Hydrogenation by a Chiral Antimony(V) Cation/Anion Pair

Jian Zhang et al.

Summary: Pnictogen-bonding catalysis based on sigma-hole interactions has been the focus of attention for synthetic chemists. A novel chiral antimony cation/anion pair was utilized to catalyze the enantioselective transfer hydrogenation of benzoxazines with remarkable efficiency and enantiocontrol potency even at 0.05 mol % loading. Investigation into the properties of the catalyst and mechanistic insights were conducted through nonlinear effect studies, 1H NMR, LC-MS, and control experiments.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Organic

Enantioselective Construction of Spirooxindole-Fused Cyclopentanes

Vojtech Docekal et al.

Summary: This study describes an asymmetric organocatalytic cascade reaction catalyzed by a simple chiral secondary amine, leading to the formation of spirooxindole-fused cyclopentanes with high enantioselectivity and synthetic utility. Further transformations of the spiro compounds were demonstrated, along with a study showing the potential biological activity of the enantioenriched products.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Review Chemistry, Multidisciplinary

Enantioselective Desymmetrization of Cyclobutanones: A Speedway to Molecular Complexity

Jan Sietmann et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Organic

Catalytic Enantioselective Synthesis of 1,4-Benzodioxepines

Xi Zou et al.

ORGANIC LETTERS (2020)

Article Chemistry, Multidisciplinary

Unusual Skeletal Reorganization of Oxetanes for the Synthesis of 1,2-Dihydroquinolines

Guannan Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Highly Enantioselective, Hydrogen-Bond-Donor Catalyzed Additions to Oxetanes

Daniel A. Strassfeld et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Organic

Tandem Suzuki Coupling/Intramolecular Oxetane Ring Opening to Form Polycyclic Ring Systems

Lindsey G. DeRatt et al.

ORGANIC LETTERS (2020)

Article Chemistry, Multidisciplinary

Bronsted Acid Ionic Liquid-Catalyzed Ring Opening of 3,3-Disubstituted Oxetanes in Water: Efficient Access to Furans and Benzofurans

Chunjie Ni et al.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2020)

Article Chemistry, Multidisciplinary

3-Aminooxetanes: versatile 1,3-amphoteric molecules for intermolecular annulation reactions

Zengwei Lai et al.

CHEMICAL SCIENCE (2020)

Article Chemistry, Multidisciplinary

Asymmetric Desymmetrization of Oxetanes for the Synthesis of Chiral Tetrahydrothiophenes and Tetrahydroselenophenes

Renwei Zhang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Organic

Mild Intramolecular Ring Opening of Oxetanes

Lindsey G. DeRatt et al.

ORGANIC LETTERS (2019)

Article Biochemistry & Molecular Biology

A Novel M1 PAM VU0486846 Exerts Efficacy in Cognition Models without Displaying Agonist Activity or Cholinergic Toxicity

Jerri M. Rook et al.

ACS CHEMICAL NEUROSCIENCE (2018)

Article Chemistry, Multidisciplinary

Palladium-Catalyzed Asymmetric Aminohydroxylation of 1,3-Dienes

Hong-Cheng Shen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Synergistic formal ring contraction for the enantioselective synthesis of spiropyrazolones

Marta Meazza et al.

CHEMICAL SCIENCE (2018)

Article Chemistry, Multidisciplinary

Organocatalytic Enantioselective Synthesis of 1,4-Dioxanes and Other Oxa-Heterocycles by Oxetane Desymmetrization

Wen Yang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Enantioselective Oxetane Ring Opening with Chloride: Unusual Use of Wet Molecular Sieves for the Controlled Release of HCl

Wen Yang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Review Chemistry, Multidisciplinary

Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

James A. Bull et al.

CHEMICAL REVIEWS (2016)

Review Chemistry, Multidisciplinary

Catalytic Enantioselective Desymmetrization Reactions to All-Carbon Quaternary Stereocenters

Xing-Ping Zeng et al.

CHEMICAL REVIEWS (2016)

Review Chemistry, Multidisciplinary

Organocatalytic enantioselective desymmetrisation

A. Borissov et al.

CHEMICAL SOCIETY REVIEWS (2016)

Article Chemistry, Multidisciplinary

Origins of Selectivity and General Model for Chiral Phosphoric Acid-Catalyzed Oxetane Desymmetrizations

Pier Alexandre Champagne et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Organic

Recent Applications of Oxetanes in the Synthesis of Heterocyclic Compounds

Christian A. Malapit et al.

JOURNAL OF ORGANIC CHEMISTRY (2015)

Article Chemistry, Medicinal

Discovery of Highly Potent Dual CysLT1 and CysLT2 Antagonist

Satoshi Itadani et al.

ACS MEDICINAL CHEMISTRY LETTERS (2014)

Article Chemistry, Medicinal

Development of Novel Benzomorpholine Class of Diacylglycerol Acyltransferase I Inhibitors

Gang Zhou et al.

ACS MEDICINAL CHEMISTRY LETTERS (2014)

Article Chemistry, Multidisciplinary

Catalytic Enantioselective Intermolecular Desymmetrization of 3-Substituted Oxetanes

Zhaobin Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Review Chemistry, Multidisciplinary

Cooperative Iron-BrOnsted Acid Catalysis: Enantioselective Hydrogenation of Quinoxalines and 2H-1,4-Benzoxazines

Steffen Fleischer et al.

CHEMISTRY-A EUROPEAN JOURNAL (2013)

Article Chemistry, Organic

[Ir(P-OP)]-Catalyzed Asymmetric Hydrogenation of Diversely Substituted C=N-Containing Heterocycles

Jose Luis Nunez-Rico et al.

ORGANIC LETTERS (2013)

Article Chemistry, Multidisciplinary

Dihydrophenanthridine: A New and Easily Regenerable NAD(P)H Model for Biomimetic Asymmetric Hydrogenation

Qing-An Chen et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

Article Chemistry, Multidisciplinary

Enantioselective Intramolecular Openings of Oxetanes Catalyzed by (salen)Co(III) Complexes: Access to Enantioenriched Tetrahydrofurans

Rebecca N. Loy et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

Article Biochemistry & Molecular Biology

Rational design of 6-(2,4-diaminopyrimidinyl)-1,4-benzoxazin-3-ones as small molecule renin inhibitors

Noel A. Powell et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2007)

Article Biochemistry & Molecular Biology

Discovery of a new class of potent, selective, and orally active prostaglandin D2 receptor antagonists

K Torisu et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2004)