4.8 Article

Copper-Catalyzed Enantioselective Oxysulfenylation of Alkenols: Synthesis of Arylthiomethyl-Substituted Cyclic Ethers

Related references

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

Catalytic enantioselective oxysulfenylation of o-vinylanilides

Arunachalam Kesavan et al.

Summary: This paper demonstrates the successful enantioselective oxysulfenylation of o-vinylanilides with N-(aryl/alkylthio)imides using Tf2NH-assisted BINAM-derived thiophosphoramide catalysis. The reaction yields diverse substituted aryl/alkylthio tethered 3,1-benzoxazines with excellent enantiomeric ratios. Additionally, the synthetic applications of benzoxazines and aryl/alkylthio moieties, as well as a transition state model for the observed enantioselectivity, are discussed.

CHEMICAL COMMUNICATIONS (2021)

Article Chemistry, Organic

Copper-Catalyzed Aminosulfonylation of O-Homoallyl Benzimidates with Sodium Sulfinates to Access Sulfonylated 1,3-Oxazines

Wei Dong et al.

Summary: A facile copper-catalyzed aminosulfonylation method has been developed for the direct synthesis of potentially bioactive 1,3-oxazines using O-homoallyl benzimidates and sodium sulfinates in the presence of tert-butyl peroxybenzoate (TBPB) and XPhos ligand. This method offers the advantages of a cheap catalyst, easily available and stable sulfone reagents, and simple operation.

ORGANIC LETTERS (2021)

Review Chemistry, Multidisciplinary

Alkoxysulfenylation of alkenes: development and recent advances

Yan Cao et al.

Summary: The direct alkoxysulfenylation of alkenes is an elegant method to construct valuable beta-alkoxy sulfides using inexpensive and abundant starting materials. This method holds significant potential and applicability in the field of synthetic transformations of alkenes.

RSC ADVANCES (2021)

Article Chemistry, Multidisciplinary

Copper-catalyzed enantioselective alkene carboetherification for the synthesis of saturated six-membered cyclic ethers

Ilyas A. Berhane et al.

Summary: The enantioselective copper-catalyzed oxidative coupling of alkenols with styrenes for the construction of dihydropyrans, isochromans, pyrans and morpholines is reported. A concise formal synthesis of a sigma(1) receptor ligand using this alkene carboetherification methodology was demonstrated. Ligand, solvent and base all impact reaction efficiency, and DFT transition state calculations were presented.

CHEMICAL COMMUNICATIONS (2021)

Review Chemistry, Multidisciplinary

Catalytic, Enantioselective Sulfenofunctionalization of Alkenes: Development and Recent Advances

Anastassia Matviitsuk et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Review Biochemistry & Molecular Biology

Thiyl Radicals: Versatile Reactive Intermediates for Cyclization of Unsaturated Substrates

Dylan M. Lynch et al.

MOLECULES (2020)

Article Chemistry, Multidisciplinary

Recent Advances in Synthesis of Chiral Thioethers

Hongyi Chen et al.

CHEMICAL RECORD (2020)

Review Biochemistry & Molecular Biology

Construction of sulfur-containing moieties in the total synthesis of natural products

Nengzhong Wang et al.

NATURAL PRODUCT REPORTS (2020)

Review Chemistry, Multidisciplinary

Recent advances in copper-catalysed radical-involved asymmetric 1,2-difunctionalization of alkenes

Zhong-Liang Li et al.

CHEMICAL SOCIETY REVIEWS (2020)

Article Chemistry, Multidisciplinary

Enantio- and Diastereoselective, Lewis Base Catalyzed, Cascade Sulfenoacetalization of Alkenyl Aldehydes

Anastassia Matviitsuk et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Chemistry, Multidisciplinary

Analysis of US FDA-Approved Drugs Containing Sulfur Atoms

Kevin A. Scott et al.

TOPICS IN CURRENT CHEMISTRY (2018)

Article Chemistry, Organic

Catalytic, Enantioselective, Intramolecular Sulfenoamination of Alkenes with Anilines

Scott E. Denmark et al.

JOURNAL OF ORGANIC CHEMISTRY (2017)

Article Chemistry, Organic

Copper-Catalyzed Oxysulfenylation of Alkenoic Acids with Benzenethiols: A Strategy to Construct Sulfenylated Lactones

Manman Chen et al.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2017)

Review Chemistry, Medicinal

Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry

Minghao Feng et al.

CURRENT TOPICS IN MEDICINAL CHEMISTRY (2016)

Article Chemistry, Physical

Effect of Substituents on the Stability of Sulfur-Centered Radicals

Isa Degirmenci et al.

JOURNAL OF PHYSICAL CHEMISTRY A (2016)

Article Chemistry, Organic

Metal-free radical thiolations mediated by very weak bases

Dens Koziakov et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2016)

Article Chemistry, Multidisciplinary

Versatile Enantioselective Synthesis of Functionalized Lactones via Copper-Catalyzed Radical Oxyfunctionalization of Alkenes

Rong Zhu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Chemistry, Multidisciplinary

Enantioselective Copper-Catalyzed Carboetherification of Unactivated Alkenes

Michael T. Bovino et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Biochemistry & Molecular Biology

Synthesis and SAR study of a novel series of dopamine receptor agonists

Rune Risgaard et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2014)

Article Chemistry, Inorganic & Nuclear

Chiral Indoline Synthesis via Enantioselective Intramolecular Copper-Catalyzed Alkene Hydroamination

Benjamin W. Turnpenny et al.

ORGANOMETALLICS (2012)

Article Chemistry, Multidisciplinary

Catalytic Asymmetric Thiofunctionalization of Unactivated Alkenes

Scott E. Denmark et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

Article Chemistry, Organic

Mechanism of SH2 Reactions of Disulfides: Frontside vs Backside, Stepwise vs Concerted

Elizabeth H. Krenske et al.

JOURNAL OF ORGANIC CHEMISTRY (2009)

Article Chemistry, Organic

2,3-Diaryl-5-ethylsulfanylmethyltetrahydrofurans as a new class of COX-2 inhibitors and cytotoxic agents

Palwinder Singh et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2008)

Article Chemistry, Multidisciplinary

Copper(II)-catalyzed enantioselective intramolecular carboamination of alkenes

Wei Zeng et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

Article Chemistry, Organic

Copper-catalyzed 1,2-hydroxysulfenylation of alkene using disulfide via cleavage of the S-S bond

Nobukazu Taniguchi

JOURNAL OF ORGANIC CHEMISTRY (2006)

Review Chemistry, Organic

Recent advances in selenocyclofunctionalization reactions

N Petragnani et al.

TETRAHEDRON (2001)