silver nitrite (selected examples).Scheme 1.6 Nitration of halides under PEG solvent.Scheme 1.7 Chemoselective nitration of alkyl halides.Scheme 1.8 Nitration of mesylates and tosylates.Scheme 1.9 Oxidation of primary amines.Scheme 1.10 Oxidation of amines using HOF·CH3CN.Scheme 1.11 Oxidation of amines using Zr(O-t-Bu)4.Scheme 1.12 Retro-Nef reaction via oximes.Scheme 1.13 Oxidation of oximes with TFAA/UHP.Scheme 1.14 Oxidation of oximes using Benz-Mo.Scheme 1.15 Oxidation of azides using HOF·CH3CN.Scheme 1.16 Reduction of nitroalkenes.Scheme 1.17 Reductive nitromethylation of aldehydes.Scheme 1.18 Nitromethylation of aryl halides.Scheme 1.19 Nitroalkylation of aryl halides.Scheme 1.20 Nitroalkanes addition to vinylepoxides under Pd(0) catalysis.
3 Chapter 2Figure 2.1 Conversion of nitroalkanes into other functionalities.Figure 2.2 Common historical procedures for the reduction of nitroalkanes to...Figure 2.3 Recent procedures for the reduction of nitroalkanes to amines.Scheme 2.1 One-pot synthesis of imines.Scheme 2.2 Synthesis of Propranolol 3.Scheme 2.3 Synthesis of threo-Dihydrosphingosine 7.Scheme 2.4 Synthesis of (−)-Denopamine 13.Scheme 2.5 Enantioselective synthesis of piperidin-2-oneScheme 2.6 Synthesis of thiourea derivative 20.Scheme 2.7 Synthesis of bicycle-γ-lactam 24.Scheme 2.8 Synthesis of (S)-Rolipram 28.
4 Chapter 3Scheme 3.1 Nef original reaction.Scheme 3.2 Nef reaction by CAN.Scheme 3.3 Nef reaction by Fe–HCl.Figure 3.1 Intermediate of Nef reaction with basic silica gel.Scheme 3.4 Nef reaction by Me3SiCl: synthesis of poly(1,3-diketones).Scheme 3.5 One-pot synthesis of (R)-2-methylcyclododecanone.Scheme 3.6 One-pot synthesis of indoles 7.Scheme 3.7 One-pot synthesis of benzofurans 11.Scheme 3.8 Synthesis of Kinamycin antibiotic analogs 16.Scheme 3.9 Synthesis of γ-lactams 23.Scheme 3.10 Synthesis of sarkomycin 28.Scheme 3.11 Synthesis of (−)-Cyclophellitol 33.Scheme 3.12 Synthesis of intermediate for Manzamine A 35.Scheme 3.13 Synthesis of (−)-Pyrenophorin 41.Scheme 3.14 Synthesis of algicidal cyclopentenone 45.Scheme 3.15 Synthesis of chiral lactone 49.Scheme 3.16 Synthesis of Isosolanone 53.Scheme 3.17 Synthesis of polycyclic aromatic structure 56.Scheme 3.18 Synthesis of (−)-Botryodiplodin 60.Scheme 3.19 Synthesis of (+)-Ibuprofen 63.
5 Chapter 4Scheme 4.1 Nitroaldol (Henry) reaction.Figure 4.1 Transformation of β-nitro alcohol.Scheme 4.2 One-pot nitroaldol reaction from haloderivatives.Figure 4.2 Nitroaldol reaction vs. nitroaldol condensation.Scheme 4.3 Nitroaldol (Henry) condensation promoted by hyperbranched polyami...Scheme 4.4 Nitroaldol reaction promoted by Al2O3 in scCO2.Scheme 4.5 One-pot nitroaldol condensation using bromonitromethane.Scheme 4.6 Nitroaldol (Henry) reaction of BrCH2NO2 under SmI2 catalysis.Scheme 4.7 Nitroaldol condensation by SG-MNP-NH2.Scheme 4.8 Synthesis of A-ring of Taxane diterpene, via the Henry reaction....Scheme 4.9 Intramolecular Henry reaction with Stryker’s reagent.Scheme 4.10 Synthesis of D-Glucosamine monosaccharides.Scheme 4.11 Synthesis of (E)-9-nitrooleic acid 17.Scheme 4.12 Synthesis of (E)-9-nitrooleic acid 20.Scheme 4.13 Synthesis of α-Cedrene 26.Scheme 4.14 Synthesis of (±)-Acoradiene 32a.Scheme 4.15 Synthesis of Lycoricidine 36.Scheme 4.16 Synthesis of 4-hydroxyheptadecan-7-one 40.Scheme 4.17 Synthesis of 14-hydroxyoctadecan-8-one 44.Scheme 4.18 Synthesis of segment 48 of Swinholide A.Scheme 4.19 Asymmetric Henry reaction by ligand A.Scheme 4.20 Synthesis of (S)-Miconazole 53.Scheme 4.21 Synthesis of (R)-Phenylephrine 57.Scheme 4.22 Synthesis of (S)-N-trans-feruloyl 61.Scheme 4.23 Synthesis of 66.Scheme 4.24 Asymmetric synthesis of (1R, 2S)-methoxamine·HCl.Scheme 4.25 Asymmetric synthesis of (S)-Toliprolol 72a, (S)-Moprolol 72b, an...Scheme 4.26 Asymmetric synthesis of (R)-Isoproterenol 76.Figure 4.3 Ligand G.Figure 4.4 Ligand H.Figure 4.5 Ligand I.Figure 4.6 Ligand J.Figure 4.7 Ligand K.Figure 4.8 Ligand La,b.Figure 4.9 Ligand Ma–g.Figure 4.10 Aza-Henry (or nitro-Mannich) reaction.Figure 4.11 Catalyst 134.Scheme 4.27 Asymmetric aza-Henry reaction with ligand N.Scheme 4.28 Asymmetric aza-Henry reaction with indium. Selected example.Scheme 4.29 Aza-Henry reaction of trifluoromethyl ketimines. Selected exampl...Scheme 4.30 Cyclization of 82a into imidazoline 84.Scheme 4.31 Asymmetric aza-Henry reaction with ligand O.Scheme 4.32 Synthesis of (S)-Levamisole 89.Scheme 4.33 Dehydrogenative aza-Henry reaction.Scheme 4.34 Three-component aza-Henry reaction via crystallization.Scheme 4.35 Reduction of amino acid. Synthesis of vicinal diamines.Scheme 4.36 Aza-Henry reaction under ligand P-Et2Zn catalysis.Scheme 4.37 Synthesis of Epiquinamide 105.Scheme 4.38 AHR under rosin-derived amine thiourea catalyst 109 and 110.Scheme 4.39 AHR under phase-transfer catalysis 113 derived from cinchona alk...Scheme 4.40 Synthesis of 1,2-diamines 115 and α-aminoester 117.Scheme 4.41 Asymmetric AHR catalyzed by thiourea-phosphonium salt (catalyst Scheme 4.42 Synthesis of chiral amino-substituted γ-lactam 124.Scheme 4.43 Synthesis of Taurine 129.Scheme 4.44 AHR under catalysts 130 and 131.Figure 4.12 Catalyst 135.Scheme 4.45 Asymmetric synthesis of 140 under catalyst 136.Scheme 4.46 Asymmetric synthesis of 145 under catalyst 141.Scheme 4.47 Asymmetric synthesis of 150 under catalyst 146.
6 Chapter 5Figure 5.1 Conjugate addition (Michael reaction).Scheme 5.1 Synthesis of diamino alcohols 4 from in situ Henry–Michael reacti...Scheme 5.2 Synthesis of methylene butyrolactones 8.Scheme 5.3 Synthesis of α,β-unsaturated nitriles 12.Scheme 5.4 Michael reaction using Amberlyst A27 as promoter.Scheme 5.5 Michael reaction using Isolute® as promoter.Figure 5.2 Structure of PS-BEMP.Scheme 5.6 One-pot Henry–Michael reaction promoted by Isolute®.Scheme 5.7 Intramolecular Michael reaction.Scheme 5.8 One-pot Michael reaction from haloderivatives.Scheme 5.9 Conjugate addition to the dienoic ester 23.Scheme 5.10 One-pot synthesis of 1,4-difuntionalized molecules from nitroalk...Scheme 5.11 Synthesis of substituted Δ1-pyrrolines 33.Scheme 5.12 Michael reaction of nitroalkanes under chiral imidazoline–tetraz...Scheme 5.13 Michael reaction of nitroalkanes under 5-pyrrolidin-2-yltetrazol...Scheme 5.14 Michael reaction of nitroalkanes catalyzed by trans-amino-prolin...Figure 5.3 α-Aminophosphonate.Scheme 5.15 Michael reaction of nitroalkanes catalyzed by Cinchona alkaloid ...Figure 5.4 Catalyst 44.Scheme 5.16 Michael reaction catalyzed by the thiourea 45.Scheme 5.17 Conjugate addition of α-nitroacetate to α,β-unsaturated ketones