Catalytic Enantioselective Entry to Triflones Featuring a Quaternary Stereocenter

Review Chemistry, Organic

Advances in Synthesis of Enantioenriched Chiral Sulfones by Enantioselective Conjugate Addition Reactions

Xiayu Liang et al.

Summary: This paper reviews the advances and state of synthesizing chiral sulfones by addition reactions, categorizing the methods by types of reaction and arranging them in chronological order.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2022)

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Article Chemistry, Multidisciplinary

Carbene-Catalyzed Enantioselective Sulfonylation of Enone Aryl Aldehydes: A New Mode of Breslow Intermediate Oxidation

Rui Deng et al.

Summary: A novel carbene-catalyzed sulfonylation reaction between enone aryl aldehydes and sulfonyl chlorides has been disclosed, leading to the efficient installation of sulfone moieties. The NHC catalyst provides activation and stereoselectivity control on a very remote site of the enone aryl aldehyde substrates. Water plays a crucial role in modulating catalyst deactivation and reactivation routes involving reactions between NHC and sulfonyl chloride.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

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Article Chemistry, Multidisciplinary

Palladium-Catalyzed Asymmetric Hydrosulfonylation of 1,3-Dienes with Sulfonyl Hydrazides

Ming-Ming Li et al.

Summary: The highly enantio- and regioselective hydrosulfonylation of 1,3-dienes with sulfonyl hydrazides was achieved using a palladium catalyst containing a monodentate chiral spiro phosphoramidite ligand, providing a practical method for synthesizing chiral allylic sulfones. Mechanistic studies indicated that the reaction proceeds through the formation of an allyl hydrazine intermediate and subsequent rearrangement to the chiral allylic sulfone product, with the enantioselectivity determined in the conversion from the intermediate to the product.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Review Chemistry, Applied

Pyrazoleamides in Catalytic Asymmetric Reactions: Recent Advances

Sara Meninno et al.

Summary: Pyrazoleamides have gained attention as reactive and practical surrogates in asymmetric catalysis, particularly in a variety of metal- and organocatalytic transformations. Their relevance has extended to photoredox catalysis and challenging stereoselective bond-forming reactions in recent years.

ADVANCED SYNTHESIS & CATALYSIS (2021)

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Article Chemistry, Multidisciplinary

Recent Progress on the Synthesis of Chiral Sulfones

Youming Huang et al.

Summary: Chiral sulfones are widely used in drugs, agricultural chemicals, chiral organic intermediates, and functional materials. The rapid development of synthetic methods for chiral sulfones in recent years is mainly attributed to the adoption of transition metal complex catalysts with chiral ligands and chiral organocatalysts.

CHEMICAL RECORD (2021)

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Article Chemistry, Organic

Continuous Flow Synthesis of α-Trifluoromethylthiolated Esters and Amides from Carboxylic Acids: a Telescoped Approach

Francesca Franco et al.

Summary: A continuous flow approach was developed for the synthesis of alpha-trifluoromethylthiolated esters and amides using commercially available arylacetic acids and N-(trifluoromethylthio)phthalimide as the electrophilic reagent. The telescoped process resulted in good overall yield and short reaction times for the formation of alpha-substituted SCF3 amides and esters.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Review Chemistry, Organic

Recent advances for the synthesis of chiral sulfones with the sulfone moiety directly connected to the chiral center

Chuanle Zhu et al.

Summary: Chiral sulfones, especially those compounds with sulfone groups directly connected to the chiral centers, are privileged building blocks in natural products and bioactive compounds. Various strategies have been developed for their asymmetric synthesis, including nucleophilic substitution, hydrosulfonation, cross-coupling reactions, and others, which are important for the synthesis of bioactive compounds.

ORGANIC CHEMISTRY FRONTIERS (2021)

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Article Chemistry, Multidisciplinary

Sulfone Group as a Versatile and Removable Directing Group for Asymmetric Transfer Hydrogenation of Ketones

Vijyesh K. Vyas et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Multidisciplinary

Palladium-Catalyzed Regio- and Enantioselective Hydrosulfonylation of 1,3-Dienes with Sulfinic Acids: Scope, Mechanism, and Origin of Selectivity

Qinglong Zhang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Chemistry, Multidisciplinary

Formal alpha-trifluoromethylthiolation of carboxylic acid derivatives via N-acyl pyrazoles

Francesca Franco et al.

CHEMICAL COMMUNICATIONS (2020)

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Article Multidisciplinary Sciences

Modular synthesis of α-fluorinated arylmethanes via desulfonylative cross-coupling

Masakazu NamboD et al.

NATURE COMMUNICATIONS (2019)

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Article Chemistry, Multidisciplinary

Copper-Catalyzed Enantioselective Construction of Tertiary Propargylic Sulfones

Jose Enrique Gomez et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Article Chemistry, Organic

Transition state analysis of an enantioselective Michael addition by a bifunctional thiourea organocatalyst

Joseph A. Izzo et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2019)

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Review Chemistry, Multidisciplinary

A continuing challenge: N-heterocyclic carbene-catalyzed syntheses of gamma-butyrolactones

Kathleen J. R. Murauski et al.

CHEMICAL SOCIETY REVIEWS (2018)

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Article Chemistry, Multidisciplinary

Organocatalytic Enantioselective Construction of Axially Chiral Sulfone-Containing Styrenes

Shiqi Jia et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Article Multidisciplinary Sciences

Selenide-catalyzed enantioselective synthesis of trifluoromethylthiolated tetrahydronaphthalenes by merging desymmetrization and trifluoromethylthiolation

Jie Luo et al.

NATURE COMMUNICATIONS (2018)

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Article Chemistry, Inorganic & Nuclear

New utility of electrophilic trifluoromethylthiolation reagents for the synthesis of a variety of triflones

Zhongyan Huang et al.

JOURNAL OF FLUORINE CHEMISTRY (2017)

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Article Chemistry, Organic

Cinchona Alkaloid-Squaramide Catalyzed Sulfa-Michael Addition Reaction: Mode of Bifunctional Activation and Origin of Stereoinduction

Jinlong Guo et al.

JOURNAL OF ORGANIC CHEMISTRY (2017)

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Article Chemistry, Organic

Rh-Catalyzed Asymmetric Hydrogenation of α-Substituted Vinyl Sulfones: An Efficient Approach to Chiral Sulfones

Liyang Shi et al.

ORGANIC LETTERS (2017)

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Article Chemistry, Organic

Stereoselective Synthesis of β-Lactam-triflones under Catalyst-Free Conditions

Zhongyan Huang et al.

ORGANIC LETTERS (2015)

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Review Chemistry, Multidisciplinary

Synthetic Methods for Compounds Having CF3-S Units on Carbon by Trifluoromethylation, Trifluoromethylthiolation, Triflylation, and Related Reactions

Xiu-Hua Xu et al.

CHEMICAL REVIEWS (2015)

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Article Chemistry, Multidisciplinary

Serendipitous Discovery of a Potent Influenza Virus A Neuraminidase Inhibitor

Sankar Mohan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

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Article Chemistry, Multidisciplinary

Stereoconvergent Arylations and Alkenylations of Unactivated Alkyl Electrophiles: Catalytic Enantioselective Synthesis of Secondary Sulfonamides and Sulfones

Junwon Choi et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

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Article Chemistry, Multidisciplinary

Enantioselective synthesis of α-nitro-δ-ketosulfones via a quinine-squaramide catalyzed conjugate addition of α-nitrosulfones to enones

Kalisankar Bera et al.

CHEMICAL COMMUNICATIONS (2013)

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Article Chemistry, Multidisciplinary

Chiral Fluorinated α-Sulfonyl Carbanions: Enantioselective Synthesis and Electrophilic Capture, Racemization Dynamics, and Structure

Gunther Hellmann et al.

CHEMISTRY-A EUROPEAN JOURNAL (2013)

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Article Chemistry, Multidisciplinary

Octupolar Derivatives Functionalized with Superacceptor Peripheral Groups: Synthesis and Evaluation of the Electron-Withdrawing Ability of Potent Unusual Groups

Cedric Rouxel et al.

CHEMISTRY-A EUROPEAN JOURNAL (2012)

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Article Chemistry, Organic

Antifungal Diterpene Alkaloids from the Caribbean Sponge Agelas citrina: Unified Configurational Assignments of Agelasidines and Agelasines

E. Paige Stout et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2012)

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Article Chemistry, Medicinal

Quinazoline Sulfonamides as Dual Binders of the Proteins B-Cell Lymphoma 2 and B-Cell Lymphoma Extra Long with Potent Proapoptotic Cell-Based Activity

Brad E. Sleebs et al.

JOURNAL OF MEDICINAL CHEMISTRY (2011)

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Article Chemistry, Medicinal

Cyclic Sulfones as Novel P3-Caps for Hepatitis C Virus NS3/4A (HCV NS3/4A) Protease Inhibitors: Synthesis and Evaluation of Inhibitors with Improved Potency and Pharmacokinetic Profiles

Francisco Velazquez et al.

JOURNAL OF MEDICINAL CHEMISTRY (2010)

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Article Chemistry, Organic

Iridium-Catalyzed, Regio- and Enantioselective Allylic Substitution with Aromatic and Aliphatic Sulfinates

Mitsuhiro Ueda et al.

ORGANIC LETTERS (2010)

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Review Chemistry, Multidisciplinary

Evolving Organic Synthesis Fostered by the Pluripotent Phenylsulfone Moiety

Ahmad El-Awa et al.

CHEMICAL REVIEWS (2009)

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Article Chemistry, Multidisciplinary

Highly Enantioselective Conjugate Additions of Aldehydes to Vinyl Sulfones

Aitor Landa et al.

CHEMISTRY-A EUROPEAN JOURNAL (2009)

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Article Multidisciplinary Sciences

α-Fluoro-α-nitro(phenylsulfonyl)methane as a fluoromethyl pronucleophile: Efficient stereoselective Michael addition to chalcones

G. K. Surya Prakash et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2009)

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Article Chemistry, Medicinal

Discovery of an Orally Bioavailable Small Molecule Inhibitor of Prosurvival B-Cell Lymphoma 2 Proteins

Cheol-Min Park et al.

JOURNAL OF MEDICINAL CHEMISTRY (2008)

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Article Chemistry, Physical

The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals

Yan Zhao et al.

THEORETICAL CHEMISTRY ACCOUNTS (2008)

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Article Chemistry, Multidisciplinary

Inverse solvent effects in carbocation carbanion combination reactions: The unique behavior of trifluoromethylsulfonyl stabilized carbanions

Stefan T. A. Berger et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

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Review Chemistry, Multidisciplinary

Synthesis, fluorescence, and two-photon absorption of a series of elongated rodlike and banana-shaped quadrupolar fluorophores: A comprehensive study of structure-property relationships

Olivier Mongin et al.

CHEMISTRY-A EUROPEAN JOURNAL (2007)

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Article Chemistry, Multidisciplinary

Highly enantioselective reactions of alpha-sulfonyl carbanions of trifluoromethyl sulfones

Shuichi Nakamura et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2007)

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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)

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Article Chemistry, Organic

Practical asymmetric synthesis of a γ-secretase inhibitor exploiting substrate-controlled intramolecular nitrile oxide-olefin cycloaddition

JP Scott et al.

JOURNAL OF ORGANIC CHEMISTRY (2006)

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Article Chemistry, Organic

Rhodium-catalyzed enantioselective conjugate addition of organoboronic acids to α,β-unsaturated sulfones

P Mauleón et al.

ORGANIC LETTERS (2004)

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Article Chemistry, Multidisciplinary

Enantioselective Michael reaction of malonates to nitroolefins catalyzed by bifunctional organocatalysts

T Okino et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2003)

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Article Chemistry, Organic

Super acidifiers:: the origin of the exceptional electron transmission capability of the SO2CF3 group in carbanion stabilization

W Goumont et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2003)

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Catalytic Enantioselective Entry to Triflones Featuring a Quaternary Stereocenter

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