The Experts below are selected from a list of 360 Experts worldwide ranked by ideXlab platform
Denis Chusov - One of the best experts on this subject based on the ideXlab platform.
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Reductive Amination in the synthesis of pharmaceuticals
Chemical Reviews, 2019Co-Authors: Oleg I Afanasyev, Denis Chusov, Dmitry L Usanov, Ekaterina A KuchukAbstract:Reductive Amination plays a paramount role in pharmaceutical and medicinal chemistry owing to its synthetic merits and the ubiquitous presence of amines among biologically active compounds. It is one of the key approaches to C-N bond construction due to its operational easiness and a wide toolbox of protocols. Recent studies show that at least a quarter of C-N bond-forming reactions in the pharmaceutical industry are performed via Reductive Amination. This Review concisely compiles information on 71 medical substances that are synthesized by Reductive Amination. Compounds are grouped according to the principle of action, which includes drugs affecting the central nervous system, drugs affecting the cardiovascular system, anticancer drugs, antibiotics, antiviral and antifungal medicines, drugs affecting the urinary system, drugs affecting the respiratory system, antidiabetic medications, drugs affecting the gastrointestinal tract, and drugs regulating metabolic processes. A general synthetic scheme is provided for each compound, and the description is focused on Reductive Amination steps. The green chemistry metric of reaction mass efficiency was calculated for all reactions.
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hydrogen free Reductive Amination using iron pentacarbonyl as a reducing agent
Organic and Biomolecular Chemistry, 2017Co-Authors: Oleg I Afanasyev, Dmitry L Usanov, Denis ChusovAbstract:We developed solvent-free Reductive Amination without an external hydrogen source using iron pentacarbonyl as a reducing agent. Neither a catalyst nor any other additives were employed. Various types of substrates are suitable for the reaction, including those with low reactivity, e.g. benzophenone. Among others, the protocol tolerates bromo-, cyano-, benzyloxy-, pyrimidyl and styryl moieties.
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ruthenium catalyzed Reductive Amination without an external hydrogen source
Organic Letters, 2015Co-Authors: Pavel N Kolesnikov, Niyaz Z Yagafarov, Dmitry L Usanov, Victor I Maleev, Denis ChusovAbstract:A ruthenium-catalyzed Reductive Amination without an external hydrogen source has been developed using carbon monoxide as the reductant and ruthenium(III) chloride (0.008–2 mol %) as the catalyst. The method was applied to the synthesis of antianxiety agent ladasten.
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Reductive Amination without an external hydrogen source
Angewandte Chemie, 2014Co-Authors: Denis Chusov, Benjamin ListAbstract:A method of Reductive Amination without an external hydrogen source is reported. Carbon monoxide is used as the reductant. The reaction proceeds efficiently for a variety of carbonyl compounds and amines at low catalyst loadings and is mechanistically interesting as it does not seem to involve molecular hydrogen.
Jianliang Xiao - One of the best experts on this subject based on the ideXlab platform.
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asymmetric Reductive Amination
ChemInform, 2015Co-Authors: Chao Wang, Jianliang XiaoAbstract:Review: recent advances in asymmetric Reductive Amination by hydrogenation, transfer hdrogenation, organocatalytic and biocatalytic reduction; 103 refs.
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fast Reductive Amination by transfer hydrogenation on water
Chemistry: A European Journal, 2013Co-Authors: Qian Lei, Chao Wang, Jianliang Xiao, Yawen Wei, Dinesh Talwar, Dong XueAbstract:Reductive Amination of vari- ous ketones and aldehydes by transfer hydrogenation under aqueous condi- tions has been developed, by using cy- clometallated iridium complexes as cat- alysts and formate as hydrogen source. The pH value of the solution is shown to be critical for a high catalytic chemoA and activity, with the best pH value being 4.8. In comparison with that in organic solvents, the reduc- tive Amination in an aqueous phase is faster, and the molar ratio of the sub- strate to the catalyst (S/C) can be set as high as 1 � 10 5 , the highest S/C value ever reported in Reductive Amination reactions. The catalyst is easy to access and the reaction is operationally simple, allowing a wide range of ke- tones and aldehydes to react with vari- ous amines in high yields. The protocol provides a practical and environmental friendly new method for the synthesis of amine compounds.
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asymmetric Reductive Amination
Topics in Current Chemistry, 2013Co-Authors: Chao Wang, Jianliang XiaoAbstract:Asymmetric Reductive Amination (ARA) affords synthetically valuable chiral amines straightforwardly. This chapter reviews the recent advances made in the area, focusing on ARA by hydrogenation, transfer hydrogenation, organocatalytic reduction, and biocatalytic reduction.
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a versatile catalyst for Reductive Amination by transfer hydrogenation
Angewandte Chemie, 2010Co-Authors: Chao Wang, Alan John Pettman, John Basca, Jianliang XiaoAbstract:Reductive Amination of a wide variety of aromatic and aliphatic ketones and aldehydes with primary and secondary amines proceeds smoothly in the presence of a novel cyclometalated Ir catalyst.
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metal bronsted acid cooperative catalysis for asymmetric Reductive Amination
Journal of the American Chemical Society, 2009Co-Authors: Chaoqun Li, Barbara Villamarcos, Jianliang XiaoAbstract:Direct Reductive Amination of a wide range of ketones has been accomplished by the cooperative catalysis of an Ir(III)-diamine complex and a chiral phosphoric acid or its conjugate base.
Matthias Otte - One of the best experts on this subject based on the ideXlab platform.
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The B(C6F5)3-Catalyzed Tandem Meinwald Rearrangement-Reductive Amination.
Organic letters, 2016Co-Authors: Martine R. Tiddens, Robertus J. M. Klein Gebbink, Matthias OtteAbstract:A system of three coupled catalytic cycles enabling the one-pot transformation of epoxides to amines via Meinwald rearrangement, imine condensation, and imine reduction is described. This assisted tandem catalysis is catalyzed by B(C6F5)3 resulting in the first tandem Meinwald rearrangement-Reductive Amination protocol. The reaction proceeds in nondried solvents and yields β-functionalized amines. In particular, β-diarylamines are obtained in high yields.
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The B(C6F5)3‑Catalyzed Tandem Meinwald Rearrangement–Reductive Amination
2016Co-Authors: Martine R. Tiddens, Robertus J. M. Klein Gebbink, Matthias OtteAbstract:A system of three coupled catalytic cycles enabling the one-pot transformation of epoxides to amines via Meinwald rearrangement, imine condensation, and imine reduction is described. This assisted tandem catalysis is catalyzed by B(C6F5)3 resulting in the first tandem Meinwald rearrangement–Reductive Amination protocol. The reaction proceeds in nondried solvents and yields β-functionalized amines. In particular, β-diarylamines are obtained in high yields
Jeanluc Renaud - One of the best experts on this subject based on the ideXlab platform.
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highly active phosphine free bifunctional iron complex for hydrogenation of bicarbonate and Reductive Amination
ChemInform, 2015Co-Authors: Trieutien Thai, Delphine S Merel, Albert Poater, Sylvain Gaillard, Jeanluc RenaudAbstract:The newly developed title complex proves efficient in the Reductive Amination of various aldehydes and ketones with primary aliphatic and aromatic amines as well as secondary amines.
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highly active phosphine free bifunctional iron complex for hydrogenation of bicarbonate and Reductive Amination
Chemistry: A European Journal, 2015Co-Authors: Trieutien Thai, Delphine S Merel, Albert Poater, Sylvain Gaillard, Jeanluc RenaudAbstract:KGaA, Weinheim.Based on a "transition metal frustrated Lewis pair" approach, a cyclopentadienone iron tricarbonyl complex has been designed and applied in the Reductive Amination and hydrogenation of bicarbonate. This well-defined phosphine-free complex displays the best activities reported to date for an iron complex in the reduction of bicarbonate into formate and in Reductive Amination
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knolker s iron complex an efficient in situ generated catalyst for Reductive Amination of alkyl aldehydes and amines
Angewandte Chemie, 2012Co-Authors: Anastassiya Pagnouxozherelyeva, Sylvain Gaillard, Nicolas Pannetier, Mbaye Diagne Mbaye, Jeanluc RenaudAbstract:An aminated series: a well-defined iron-catalyzed Reductive Amination reaction of aldehydes and ketones with aliphatic amines using molecular hydrogen is presented. Under mild conditions, good yields for a broad range of alkyl ketones as well as aldehydes were achieved.
Martine R. Tiddens - One of the best experts on this subject based on the ideXlab platform.
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The B(C6F5)3-Catalyzed Tandem Meinwald Rearrangement-Reductive Amination.
Organic letters, 2016Co-Authors: Martine R. Tiddens, Robertus J. M. Klein Gebbink, Matthias OtteAbstract:A system of three coupled catalytic cycles enabling the one-pot transformation of epoxides to amines via Meinwald rearrangement, imine condensation, and imine reduction is described. This assisted tandem catalysis is catalyzed by B(C6F5)3 resulting in the first tandem Meinwald rearrangement-Reductive Amination protocol. The reaction proceeds in nondried solvents and yields β-functionalized amines. In particular, β-diarylamines are obtained in high yields.
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The B(C6F5)3‑Catalyzed Tandem Meinwald Rearrangement–Reductive Amination
2016Co-Authors: Martine R. Tiddens, Robertus J. M. Klein Gebbink, Matthias OtteAbstract:A system of three coupled catalytic cycles enabling the one-pot transformation of epoxides to amines via Meinwald rearrangement, imine condensation, and imine reduction is described. This assisted tandem catalysis is catalyzed by B(C6F5)3 resulting in the first tandem Meinwald rearrangement–Reductive Amination protocol. The reaction proceeds in nondried solvents and yields β-functionalized amines. In particular, β-diarylamines are obtained in high yields
