☆ 4.4 Article

Chiral amines in the diastereoselective Mannich-related multicomponent synthesis of diarylmethylamines, 1,2-diarylethylamines, and β-arylethylamines

TETRAHEDRON (2010)

Journal

TETRAHEDRON

Volume 66, Issue 52, Pages 9902-9911

Publisher

PERGAMON-ELSEVIER SCIENCE LTD

DOI: 10.1016/j.tet.2010.10.058

Keywords

Multicomponent reactions; Organozinc compounds; Diastereoselectivity; Cobalt; Zinc

Categories

Chemistry, Organic

Funding

CNRS
University Paris-Est Creteil

Ask authors/readers for more resources

Protocol

Community support

Reagent

Community support

Abstract

The multicomponent synthesis of diarylmethylamines, 1,2-diarylethylamines and beta-arylethylamines has been undergone starting from aryl- or benzylzinc reagents, aldehydes, and primary or secondary chiral amines. Good to high diastereoselectivities have been obtained from both L-proline ester derivatives 1 and (+/-)-trans-1-allyl-2,5-dimethylpiperazine (4). The use of R-(+)-1-phenylethylamine (7) provides important diastereoisomeric excesses (similar to 60%) in conjunction with very high chemical yields. This work constitutes a preliminary entry to the intended development of a more flexible reaction system, involving easily cleavable chiral amines. (C) 2010 Elsevier Ltd. All rights reserved.

Authors

I am an author on this paper

Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.4

Not enough ratings

Secondary Ratings

Novelty

-

Significance

-

Scientific rigor

-

Rate this paper

Recommended

Article Chemistry, Applied

Multicomponent Reaction of Aliphatic Organozinc Reagents, Acrylates and Acyl chlorides: Synthesis of & alpha;-Substituted & beta;-Ketoesters

Marine Pinaud, Walid Baba Hamed, Marc Presset, Erwan Le Gall

Summary: An uncatalyzed three-component reaction utilizing aliphatic organozinc reagents is introduced for the synthesis of α-substituted β-ketoesters. This versatile method involves a formal conjugate addition/crossed-Claisen domino reaction between organozinc, acrylate, and acyl chloride, enabling the facile preparation of the desired products under mild conditions. The three-component coupling can also be performed using alkyl iodides, providing a simpler procedure. Experimental findings suggest a possible polar concerted mechanism involving at least two organozinc compounds in the transition state.

ADVANCED SYNTHESIS & CATALYSIS (2023)

Add to Collection

Article Biochemistry & Molecular Biology

Letter to the editor regarding Effectiveness and safety of 0.5% timolol solution in the treatment of pyogenic granuloma: A randomised, double-blind and placebo-controlled study

Marine Pinaud, Marc Presset, Erwan Le Gall

Summary: Catalyst-free multicomponent reactions using mixed alkylzinc reagents with Michael acceptors and carbonyl compounds or activated imines are explored. This approach enables the efficient synthesis of varied beta-hydroxycarbonyl compounds by employing primary, secondary, and tertiary alkylzinc reagents generated from corresponding iodoalkanes in acetonitrile. The reaction with imines exhibits contrasting results due to direct addition of the organozinc compound to the C=N bond. Mechanistic studies suggest a polar nature rather than a radical character for this reaction.

MOLECULES (2023)

Add to Collection

Article Chemistry, Applied

Iron-Catalyzed Radical Zincations of Alkyl Iodides

Alisa S. Sunagatullina, Ferdinand H. Lutter, Konstantin Karaghiosoff, Paul Knochel

Summary: We have developed a new iron-catalyzed reaction for converting alkyl iodides into alkylzinc iodides. The reaction exhibits diastereoselective ring closures when a remote double bond is present at position 5. Furthermore, the resulting zinc reagents can be further reacted with various electrophiles under copper or palladium catalysis to provide diverse polyfunctional products.

ADVANCED SYNTHESIS & CATALYSIS (2022)

Add to Collection

Review Chemistry, Medicinal

The application of isatin-based multicomponent-reactions in the quest for new bioactive and druglike molecules

Pedro Brandao, Carolina Marques, Anthony J. Burke, Marta Pineiro

Summary: Oxindole derivatives are known for their vast biological activities in Medicinal Chemistry. Recent studies on the preparation of oxindole derivatives using isatin-based multicomponent reactions have advanced the generation of druglike libraries with wide scaffold diversity.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Recent Advances in Multicomponent Reactions with Organic and Inorganic Sulfur Compounds

Qinqin Tang, Xianjie Yin, Ratnakar Reddy Kuchukulla, Qingle Zeng

Summary: This review summarizes recent advances in multicomponent reactions involving sulfur components, highlighting the use of various sulfur compounds as reactants.

CHEMICAL RECORD (2021)

Add to Collection

Article Chemistry, Organic

Facile Synthesis of Spirocyclic Lactams via [3+2] and [3+3] Aza-Annulation Reactions

Davit Hayrapetyan, Valeriya Stepanova

Summary: In this study, spirocyclic pyrrolidones and piperidones were synthesized via [3+2]- and [3+3]-aza-annulation reactions starting from readily available alpha-ketolactones and alpha-ketolactams. The annulation reactions proceeded with good yields and excellent diastereoselectivity, creating one C-C and two C-N bonds, as well as three new stereocenters in a fast and efficient manner.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Add to Collection

Article Chemistry, Physical

Radical Cascade Multicomponent Minisci Reactions with Diazo Compounds

Yong-Liang Su, Geng-Xin Liu, Luca De Angelis, Ru He, Ammar Al-Sayyed, Kirk S. Schanze, Wen-Hao Hu, Huang Qiu, Michael P. Doyle

Summary: This study demonstrates the efficient generation of functionalized derivatives through photocatalyzed multicomponent reactions using nitrogen aromatic heterocycles, alkenes, and diazo compounds. The reaction shows high functional group tolerance and exacting regioselectivities. Mechanistic studies, including photophysical measurements, provide insights into this radical cascade reaction.

ACS CATALYSIS (2022)

Add to Collection

Review Biochemistry & Molecular Biology

Multicomponent Reactions between Heteroatom Compounds and Unsaturated Compounds in Radical Reactions

Akiya Ogawa, Yuki Yamamoto

Summary: In this mini-review, we propose a concept for designing multicomponent reactions based on sequential radical reactions. We focus on the photolysis of interelement compounds to generate heteroatom-centered radicals and study their addition to unsaturated compounds. The background, basic concepts, and methodology for constructing multicomponent radical reactions are discussed, followed by examples of reactions involving different combinations of interelement compounds and unsaturated compounds, as well as intramolecular cyclization processes.

MOLECULES (2023)

Add to Collection

Article Chemistry, Organic

Nickel-Catalyzed Cross-Electrophile Coupling Reactions between Allylic Acetates and gem-Difluorovinyl Tosylate

Xiaochun He, Jiangjun Liu, Gang Chen, Baojian Xiong, Xue Xiao, Lei Chen, Xuemei Zhang, Lin Dong, Xuelei Ma, Zhong Lian

Summary: A nickel-catalyzed cross-electrophile coupling of allylic acetates and gem-difluorovinyl tosylate has been developed. This reaction enables the synthesis of allylic gem-difluoroolefins via C(sp(3))-C(sp(2)) cross-electrophile coupling and proceeds under mild reaction conditions, providing a variety of allylic gem-difluorovinyl arenes in moderate to good yields. Mechanistic studies reveal the involvement of two different Ni(0)/Ni(II) catalytic cycles.

ORGANIC LETTERS (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Automated Quantification of Hydroxyl Reactivities: Prediction of Glycosylation Reactions

Chun-Wei Chang, Mei-Huei Lin, Chieh-Kai Chan, Kuan-Yu Su, Chia-Hui Wu, Wei-Chih Lo, Sarah Lam, Yu-Ting Cheng, Pin-Hsuan Liao, Chi-Huey Wong, Cheng-Chung Wang

Summary: The acceptor nucleophilic constants (Aka) database quantifies the nucleophilicity of hydroxyl groups in glycosylation reactions, accurately predicting stereoselectivity and yield.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Add to Collection

Article Chemistry, Applied

A Simple Preparation of Alkylzinc Reagents Compatible with Carbonyl Functions

Pauline Schiltz, Mengyu Gao, Corentin Ludwig, Corinne Gosmini

Summary: In this study, a direct method for preparing alkylzinc compounds from functionalized alkyl bromides using cobalt catalysis under mild conditions was reported. The reaction is stable under air and moisture conditions, making it an accessible procedure. Various functional groups on primary and secondary alkyl bromides, including esters, cyano, and halogens, were well-tolerated, resulting in high yields of the corresponding alkylzinc compounds. The alkylzinc derivatives were successfully applied in palladium-catalyzed Negishi cross-coupling with different functionalized aryl bromides, demonstrating the efficiency and robustness of the methodology.

ADVANCED SYNTHESIS & CATALYSIS (2023)

Add to Collection

Review Chemistry, Multidisciplinary

Multicomponent Reactions (MCRs) with o-Quinone Methides

Maria Tereza M. Martins, Flaviana Rodrigues F. Dias, Raphael Silva M. de Moraes, Marcos Felipe da Silva, Kaio R. Lucio, Karin D'Oliveira Goes, Patrick A. do Nascimento, Andre S. S. da Silva, Vitor F. Ferreira, Anna C. Cunha

Summary: This article provides an overview of multicomponent reactions (MCRs) that involve ortho-quinone methide intermediates (o-QM) and discusses their applications in organic synthesis and biological processes. QMs are generated through eliminative processes or photochemical reactions and can undergo various types of reactions.

CHEMICAL RECORD (2022)

Add to Collection

Article Chemistry, Physical

Cobalt-Catalyzed Multicomponent Carbonylation of Olefins: Efficient Synthesis of β-Perfluoroalkyl Imides, Amides, and Esters

Yaxin Wang, Peng Wang, Helfried Neumann, Matthias Beller

Summary: A general and broadly applicable cobalt-catalyzed multicomponent 1,2-perfluoroalkylation carbonylation of alkenes has been developed, allowing the synthesis of beta-perfluoroalkyl-substituted amides, esters, and related derivatives in a one-pot manner. The method was also demonstrated to have application potential in the synthesis of pharmaceuticals and biologically active molecules, enabling the regioselective increase of molecular complexity of olefins toward functionalized perfluoroalkylated building blocks.

ACS CATALYSIS (2023)

Add to Collection

Article Chemistry, Multidisciplinary

Direct Organometallic Synthesis of Carboxylate Intercalated Layered Zinc Hydroxides for Fully Exfoliated Functional Nanosheets

Said A. Said, Christopher S. Roberts, Ja Kyung Lee, Milo S. P. Shaffer, Charlotte K. Williams

Summary: Intercalation of carboxylate into layered zinc hydroxides can be achieved directly at room temperature, resulting in crystalline, soluble, and functionalized materials. This direct synthesis method leads to high yields of exfoliated monolayer nanosheets, with high solubilities in alcohols and water. By altering the carboxylate ligand, functional groups suitable for post-synthetic modification or for detection by fluorescence are also introduced.

ADVANCED FUNCTIONAL MATERIALS (2021)

Add to Collection

Article Chemistry, Applied

Synthesis of 1,4-Dicarbonyl Compounds via Visible-Light-Induced Decarboxylative Radical Cascade Reactions

Zhiyou Su, Jia Zhang, Hou-Wen Lin, Hongze Liao

Summary: We have developed a method for the synthesis of 1,4-dicarbonyl compounds using light-activated electron donor-acceptor (EDA) complexes. This method involves the photoactivation of EDA complexes formed by carboxylic acid derivatives, triphenylphosphine, and sodium iodide, leading to single-electron reduction. The subsequent decarboxylation fragmentation generates nucleophilic alkyl free radicals, which can react with electron-deficient and electron-rich olefins.

ADVANCED SYNTHESIS & CATALYSIS (2023)

Add to Collection

Article Electrochemistry

A Graphite Powder Cavity Cell as an Efficient Tool of Sustainable Chemistry: Electrocatalytic Homocoupling of 2-Halopyridines

Jadson L. Oliveira, El-Wan Le Gall, Stephane Sengmany, Eric Leonel, Pierre Dubot, Pierre Cenedese, Marcelo Navarro

ELECTROCHIMICA ACTA (2015)

Add to Collection

Article Chemistry, Medicinal

Synthesis of 2,3-di- and 2,2,3-trisubstituted-3-methoxycarbonyl-γ-butyrolactones as potent antitumor agents

Camille Le Floch, Erwan Le Gall, Stephane Sengmany, Patrice Renevret, Eric Leonel, Thierry Martens, Thierry Cresteil

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2015)

Add to Collection

Article Chemistry, Organic

Selective mono-amination of dichlorodiazines

Stephane Sengmany, Julie Lebre, Ewan Le Gall, Eric Leonel

TETRAHEDRON (2015)

Add to Collection

Article Chemistry, Organic

Beneficial Effects of Electrochemistry in Cross-Coupling Reactions: Electroreductive Synthesis of 4-Aryl- or 4-Heteroaryl-6-pyrrolylpyrimidines

Stephane Sengmany, Stephane Vasseur, Abdelmoumen Lajnef, Erwan Le Gall, Eric Leonel

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2016)

Add to Collection

Article Chemistry, Organic

Nickel-Catalyzed Electrochemical Reductive Homocouplings of Aryl and Heteroaryl Halides: A Useful Route to Symmetrical Biaryls

Rima Rahil, Stephane Sengmany, Erwan Le Gall, Eric Leonel

SYNTHESIS-STUTTGART (2018)

Add to Collection

Article Chemistry, Organic

A mild electroassisted synthesis of (hetero)arylphosphonates

Stephane Sengmany, Anthony Ollivier, Erwan Le Gall, Eric Leonel

ORGANIC & BIOMOLECULAR CHEMISTRY (2018)

Add to Collection

Article Chemistry, Organic

Pd-Catalyzed Chemoselective Cross-Coupling Reaction of Triaryl- or Triheteroarylbismuth Compounds with 3,6-Dihalopyridazines

Karene Urgin, Christophe Aube, Muriel Pipelier, Virginie Blot, Christine Thobie-Gautier, Stephane Sengmany, Jacques Lebreton, Eric Leonel, Didier Dubreuil, Sylvie Condon

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2013)

Add to Collection

Article Chemistry, Organic

An Electrochemical Nickel-Catalyzed Arylation of 3-Amino-6-Chloropyridazines

Stephane Sengmany, Arnaud Vitu-Thiebaud, Erwan Le Gall, Sylvie Condon, Eric Leonel, Christine Thobie-Gautier, Muriel Pipelier, Jacques Lebreton, Didier Dubreuil

JOURNAL OF ORGANIC CHEMISTRY (2013)

Add to Collection

Article Chemistry, Inorganic & Nuclear

Mannich-like three-component synthesis of α-branched amines involving organozinc compounds: ReactIR monitoring and mechanistic aspects

Erwan Le Gall, Stephane Sengmany, Caroline Haurena, Eric Leonel, Thierry Martens

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2013)

Add to Collection

Article Chemistry, Multidisciplinary

Bottom-up preparation of MgH2 nanoparticles with enhanced cycle life stability during electrochemical conversion in Li-ion batteries

Yassine Oumellal, Claudia Zlotea, Stephane Bastide, Christine Cachet-Vivier, Eric Leonel, Stephane Sengmany, Eric Leroy, Luc Aymard, Jean-Pierre Bonnet, Michel Latroche

NANOSCALE (2014)

Add to Collection

Article Chemistry, Physical

Tunable synthesis of (Mg-Ni)-based hydrides nanoconfined in templated carbon studied by in situ synchrotron diffraction

Claudia Zlotea, Fermin Cuevas, Jerome Andrieux, Camelia Matei Ghimbeu, Eric Leroy, Eric Leonel, Stephane Sengmany, Cathie Vix-Guterl, Roger Gadiou, Thierry Martens, Michel Latroche

NANO ENERGY (2013)

Add to Collection

Article Chemistry, Medicinal

Synthesis and biological evaluation of 3-amino-, 3-alkoxy- and 3-aryloxy-6-(hetero)arylpyridazines as potent antitumor agents

Stephane Sengmany, Mathilde Sitter, Eric Leonel, Erwan Le Gall, Gervaise Loirand, Thierry Martens, Didier Dubreuil, Florian Dilasser, Morgane Rousselle, Vincent Sauzeau, Jacques Lebreton, Muriel Pipelier, Remy Le Guevel

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2019)

Add to Collection

Article Chemistry, Organic

Nickel-Catalyzed Electrosynthesis of Aryl and Vinyl Phosphinates

Farah Daili, Abdelhakim Ouarti, Marine Pinaud, Ibtihal Kribii, Stephane Sengmany, Erwan Le Gall, Eric Leonel

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

Add to Collection

Article Chemistry, Organic

Direct Phosphonylation of N-Carbamate-tetrahydroisoquinoline by Convergent Paired Electrolysis

Anthony Ollivier, Stephane Sengmany, Marine Rey, Thierry Martens, Eric Leonel

SYNLETT (2020)

Add to Collection

Article Chemistry, Organic

Controlled decomposition of SF6 by electrochemical reduction

Sebastien Bouvet, Bruce Pegot, Stephane Sengmany, Erwan Le Gall, Eric Leonel, Anne-Marie Goncalves, Emmanuel Magnier

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2020)

Add to Collection

Article Chemistry, Organic

Facile synthesis of quinoxaline catalyzed by iron-based carbon material in water

Fuying Zhu, Yamei Lin

Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.

TETRAHEDRON (2024)

Add to Collection

Article Chemistry, Organic

Simple approach towards phosphorus-substituted spiro 1,3,4-thiadiazolines

Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova

Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.

TETRAHEDRON (2024)

Add to Collection

Article Chemistry, Organic

Recent advances in the synthesis of 2-cyclopentenones

Jisna Jose, Thomas Mathew

Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.

TETRAHEDRON (2024)

Add to Collection

© Peeref 2019-2024. All rights reserved.