Methodologies in Amine Synthesis. Группа авторов
of cyanide to alkylidene mal...Scheme 6.23 Enantioselective addition of nitromethane to 74 catalyzed by entScheme 6.24 Synthesis of pregabalin on kilogram scale via enantioselective c...Scheme 6.25 Enantioselective additions of acetaldehyde to nitroalkene 56 und...Scheme 6.26 One‐pot synthesis of pregabalin by a “Michaelase” enantioselecti...Scheme 6.27 Simplified reaction pathway, intermediates, and transition state...Scheme 6.28 Addition of malonates to nitroalkene 56. Selected bifunctional c...Scheme 6.29 Downstream routes to pregabalin from catalytic product 87.Scheme 6.30 Typical preparation of nitroalkene 56 vs. flow chemistry approac...Scheme 6.31 Three‐component approach to 87 by the multisite hybrid catalyst Scheme 6.32 Enantioselective additions of Meldrum's acid to nitroalkene 56 c...Scheme 6.33 Telaprevir and synthetic approaches to its bicyclic amino acid c...Scheme 6.34 Synthesis of N‐benzyl telaprevir core 111 based on quinidine 103Scheme 6.35 Retrosynthetic approaches to the telaprevir core 98: desymmetriz...Scheme 6.36 Enantioselective approach to telaprevir core 98 by chiral masked...Scheme 6.37 PTC in enantioselective conjugate additions of benzophenone glyc...Scheme 6.38 PTC addition of benzophenone glycinate imine 122 with binaphthyl...Scheme 6.39 PTC addition of benzophenone imine glycinate 122 to 114 catalyze...Scheme 6.40 Alternative glycinate imine substrates 133 and 136 applied to th...Scheme 6.41 Aminocatalytic additions of 2‐amidomalonates 138 and 139 to cycl...Scheme 6.42 Aminocatalytic addition of ethyl nitroacetate 142 to cyclopent‐1...Scheme 6.43 Aminocatalytic conjugate additions of nitromethane to cyclopent‐...Scheme 6.44 Conversion of the γ‐nitroaldehyde 145 to the...Scheme 6.45 Conversion of the γ‐nitroaldehyde adduct 145 to the...Scheme 6.46 5‐(Trifluoromethyl)‐2‐isoxazoline veterinary drugs.Scheme 6.47 Nissan Chemical Industry approach to the 5‐(trifluoromethyl)‐2‐i...Scheme 6.48 Enantioselective preparation of 5‐(trifluoromethyl)‐2‐isoxazolin...Scheme 6.49 Proposed reaction pathway and transition‐state model A with a ci...Scheme 6.50 Application of the PTC 5‐(trifluoromethyl)‐2‐isoxazoline formati...Scheme 6.51 Application of the PTC isoxazoline forming reaction to azetidine...Scheme 6.52 Large‐scale examples of the utilization of catalyst 172 in (S)‐a...Scheme 6.53 PTC enantioselective reaction with Syngenta's candidates: select...Scheme 6.54 Dimeric quininium catalysts 186, 187 in the diastereoselective i...
7 Chapter 7Scheme 7.1 Biocatalytic strategies for chiral amine synthesis. Opine dehydro...Scheme 7.2 Evolution of the substrate scope of the monoamine oxidase from As...Scheme 7.3 Enzymatic cascades involving MAO‐N variants for the preparation o...Scheme 7.4 Chemoenzymatic cascades involving MAO‐N variants for the preparat...Scheme 7.5 CHAO variants in the biocatalytic deracemization of THQs.Scheme 7.6 6‐HDNO wild‐type (black) and D350L/E352D (blue) cyclic amine subs...Scheme 7.7 Difference between reactions catalyzed by AADH and AmDH.Scheme 7.8 Selected substrate scope of the original AmDH variants developed ...Scheme 7.9 Examples of preparative scale reactions using natural AmDH.Scheme 7.10 Longer chain ketones accepted by the pocket‐expanded AmDH descri...Scheme 7.11 Scale‐up reductive amination of 2‐phenoxypropanone. CFE, cell‐fr...Scheme 7.12 Preparative scale biosynthesis of benzylic amines.Scheme 7.13 AmDH synthesis of intermediate for ethambutol.Scheme 7.14 Biocatalytic hydrogen borrowing cascade for chiral amine synthes...Scheme 7.15 Sequential dihydroxylation/hydrogen borrowing amino‐hydroxylatio...Scheme 7.16 Imine reductases in biosynthesis.Scheme 7.17 Enantioselective reduction of 2‐methylpyrroline.Scheme 7.18 Further Mitsukura IRED transformations.Scheme 7.19 IREDs in biocatalytic cascade synthesis.Scheme 7.20 IREDs in chemoenzymatic synthesis.Scheme 7.21 IRED‐catalyzed reductive amination reactions.Scheme 7.22 Applications of reductive aminases in amine alkylation cascades....Scheme 7.23 Reductive aminase‐catalyzed step in the synthesis of GSK2879552....Scheme 7.24 P411‐catalyzed intramolecular C–H amination.Scheme 7.25 Applications of engineered cytochrome P411 biocatalysts for chir...
8 Chapter 8Figure 8.1 Overview of the various methods to identify and quantify amino gr...Figure 8.2 (a) Cycloaddition of azomethine ylides to C60. (b) Arylation reac...Figure 8.3 (a) Reaction pathway for obtaining water‐soluble ammonium‐modifie...Figure 8.4 (a) Synthetic protocol for the MW‐induced double functionalizatio...Figure 8.5 (a) Functionalization of graphene via 1,3‐dipolar cycloaddition a...Figure 8.6 (a) Synthetic protocol for the production of water‐soluble amino ...Figure 8.7 Schematic illustration for the exfoliation of graphite through ba...Figure 8.8 Transmission electron micrographs of carbon nanohorns: (a) close‐...Figure 8.9 TEM images of triamide–NH conjugate in a series of bent conformat...Figure 8.10 TEM micrograph of 10 nm diameter nanodiamond.Figure 8.11 TEM images of carbon nano‐onions.Figure 8.12 Amino functionalization of CNO by (a) cycloaddition reaction on ...Figure 8.13 Role of amine precursors in the synthesis of CD. Depending on th...Figure 8.14 Examples of doping strategies to tailor the properties of NCDs d...Figure 8.15 Examples of nanoconjugates obtained from the coupling of functio...Figure 8.16 Schematic representations of 2D‐SAM, (a) amine head groups ancho...Figure 8.17 Schematic representation of the strategy described in Ref. [147]...Figure 8.18 Reaction pathways in sulfur–octylamine solution at 130 °C.Figure 8.19 Relative displacement potency labeled with the percentage of Lew...Figure 8.20 Representative TEM images for oleylamine‐based synthesis of gold...Figure 8.21 (a) TEM images of the concave Pt nanocrystals. (b) SEM image of ...Figure 8.22 Assembly steps for siRNA/PEI/PAH‐Cit/AuNP–CS complexes and pH‐re...
9 Chapter 9Figure 9.1 (a) Chitin and (b) cellulose structures.Figure 9.2 One‐pot synthesis of ADS from chitin.Figure 9.3 Conversion of NAG to AcGly catalyzed by Ru/C.Figure 9.4 Synthesis of ADI from ADS.Figure 9.5 Synthesis of 3A5AF from NAG.Figure 9.6 Direct conversion of chitin into 3A5AF.Figure 9.7 Structures of nitrogen compounds obtained from 3A5AF.Figure 9.8 Selective synthesis of deoxyfructosazine and fructosazine from D‐...Figure 9.9 Hydrogenation–decarbonylation of natural amino acids.Figure 9.10 Proposed mechanism for the metal‐free decarboxylation of amino a...Figure 9.11 Synthesis of primary amines by decarboxylation of amino acids....Figure 9.12 Synthesis of formamides by tandem decarboxylation–N‐formylation ...Figure 9.13 Reductive aminolysis of glucose into C2‐diamines.Figure 9.14 Synthesis of alkanolamines and ethylene diamines from glycolalde...Figure 9.15 Direct hydroxyethylation of amines by carbohydrates.Figure 9.16 Synthesis of HMMP from DHA.Figure 9.17 Proposed mechanism for the synthesis of HMMP.Figure 9.18 One‐pot synthesis of 2‐methyl pyrazine from glucose.Figure 9.19 One‐pot synthesis of furfurylamines from xylose.Figure 9.20 One‐pot synthesis of furfurylamines from xylose catalyzed by HRe...Figure 9.21 One‐pot conversion of xylan into furfurylamines.Figure 9.22 One‐pot synthesis of furfurylamines from xylan.Figure 9.23 Reductive amination of 5‐HMF catalyzed by Ru(DMP)2Cl2.Figure 9.24 Synthesis of BHMFA from 5‐HMF.Figure 9.25 Synthesis of BAMF from 5‐HMF.Figure 9.26 Synthesis of BAMF from DFF catalyzed by Rh/HZSM‐5.Figure 9.27 One‐pot conversion of xylose and xylan into α....Figure 9.28 One‐pot synthesis of α‐aminophosphonates from xylose and xylan....Figure 9.29 Synthesis of α‐aminophosphonates from 5‐HMF.Figure 9.30 Synthesis of 3,4‐dihydropyrimidin‐2‐ones from 5‐HMF.Figure 9.31 Synthesis of 2‐hydroxymethyl‐5‐methylpyrroles from 5‐HMF.Figure 9.32 Synthesis of pyrrolidinones and pyrrolidines from levulinic acid...Figure 9.33 Synthesis of a pyrrolidine from glucose catalyzed by an iridium ...Figure 9.34 Synthesis of pseudopeptides from levulinic acid.Figure 9.35 Synthesis of aminoketones, N‐formamides, and N‐methyl amines fro...Figure 9.36 Synthesis of alanine from glycerol.Figure 9.37 Proposed mechanism for the synthesis of alanine from glycerol....Figure 9.38 Synthesis of α‐amino acids from α‐hydroxy acids.Figure 9.39 Synthesis of aromatic N,N‐dimethyl tertiary amines from li...Figure 9.40 Synthesis 3,4‐dialkoxyanilines from 4‐propylguaiacol.Figure 9.41 Synthesis of 3,4‐dialkoxyanilines from 4‐propylguaiacol and 4‐pr...Figure 9.42 Synthesis of aminoalkylphenol derivatives and benzazepines from ...Figure 9.43 Catalytic amination of dihydroconiferyl and dihydrosinapyl alcoh...Figure 9.44 Synthesis of lignin‐derived tetrahydro‐2‐benzazepines in deep eu...Figure 9.45 N‐mono‐alkylation of aromatic and aliphatic amines with triglyce...Figure 9.46 Synthesis of fatty amines from triglycerides.Figure 9.47 Synthesis of fatty amides and nitriles from triglycerides.Figure 9.48 Synthesis of long‐chain diamines from long‐chain diols by direct...
10 Chapter 10Scheme 10.1 Historic strategies for the synthesis of aromatic amines.Scheme 10.2 Transition‐metal‐based methodologies for the preparation of arom...Scheme 10.3 (a) Ullmann's (1903) and (b) Goldberg's (1906) initial reports o...Scheme 10.4 Anticipated mechanism of the