Methodologies in Amine Synthesis. Группа авторов

3.41 Visible‐light‐mediated CDC amination of phenols and acyclic diar...Scheme 3.42 Electro‐oxidative para‐selective C–H/N–H cross‐coupling with hyd...Scheme 3.43 Selective C–H amination of heteroarenes with azoles via an organ...Scheme 3.44 Electrochemical oxidative C–H/N–H cross‐couplings for C—N bond f...Scheme 3.45 Electro‐oxidative C–H azolation of phenol and aniline derivative...Scheme 3.46 Enantioselective amination via PCET followed by stereo‐controlle...Scheme 3.47 Electrochemical intermolecular oxidative C(sp³)–H/N–H cross‐coup...

      4 Chapter 4Figure 4.1 Propargylamines: synthetic methods and drugs containing a proparg...Scheme 4.1 Chiral ligands used in asymmetric A³ coupling reactions.Scheme 4.2 Li's approach to the enantioselective synthesis of propargylamine...Scheme 4.3 Enantioselective A³ coupling approaches to propargylamines.Scheme 4.4 Knochel's enantioselective synthesis of propargylamines.Scheme 4.5 Proposed mechanism for the (R)‐(+)‐Quinap‐catalyzed A³ coupling....Scheme 4.6 Synthesis of propargylamines using (S)‐StackPhos ligand.Scheme 4.7 Aponick's strategy for the asymmetric synthesis of 3‐amino skippe...Scheme 4.8 Asymmetric synthesis of propargylamines using the StackPhim ligan...Scheme 4.9 Asymmetric synthesis of propargylamines using the UCD‐Phim L11....Scheme 4.10 Asymmetric synthesis of propargylamines using ligand L12.Scheme 4.11 Synthesis of propargylamines using Pybox ligands L13 and L14....Scheme 4.12 Proposed mechanism for the synthesis of propargylamines using Py...Scheme 4.13 Nishibayashi's approaches to propargylamines.Scheme 4.14 Hu's synthesis of propargylamines using chiral tridentate P,N,N ...Scheme 4.15 Use of a Ni(cod)₂/L19 complex in the asymmetric synthesis of pro...Scheme 4.16 Synthesis of propargylamines from ethynyl epoxides.Scheme 4.17 Asymmetric synthesis of propargylamines from lactones and cyclic...Scheme 4.18 Asymmetric synthesis of propargylamines from enamines.Scheme 4.19 Proposed mechanism for the CuBr/Quinap L6‐catalyzed synthesis of...Scheme 4.20 Synthesis of propargylamines via Rh/L23‐catalyzed enantioselecti...Scheme 4.21 Enantioselective hydrogenation of the alkynyl‐substituted enamid...Scheme 4.22 Chemoselective biomimetic hydrogenation of fluorinated alkynyl‐k...Scheme 4.23 Proposed mechanism for the reduction of ketimines.Scheme 4.24 Rhodium‐catalyzed hydrogenation of alkynyl–aryl hydrazones.Scheme 4.25 Synthesis of cyclic propargylamines via cobalt‐catalyzed intramo...Scheme 4.26 Mechanism of the cobalt‐catalyzed intramolecular cyclization.Scheme 4.27 Synthesis of chiral 2‐alkynyl‐indolines and chiral heterocyclic ...Scheme 4.28 Synthesis of cyclic propargylamines via intramolecular nitrene i...Scheme 4.29 CAL‐B‐catalyzed enzymatic kinetic resolution of 1‐aryl‐propargyl...Scheme 4.30 Enzymatic kinetic resolution of propargylamines using penicillin...Scheme 4.31 Synthesis of propargylamines using ω‐transaminases.Scheme 4.32 Synthesis of propargylamines through the combination of alcohol ...Scheme 4.33 Reductase‐biocatalyzed synthesis of propargylamines.Scheme 4.34 MAO‐N/Au chemoenzymatic synthesis of cyclic propargylamines.Scheme 4.35 Rueping's photoredox approach to propargylamines.Scheme 4.36 Photoredox synthesis of propargylamines using ethynylbenziodoxol...Scheme 4.37 Synthesis of propargylamines via photoredox decarboxylative alky...Scheme 4.38 Copper photoredox‐catalyzed A³ coupling of arylamines, terminal ...Scheme 4.39 Brønsted acid‐catalyzed Mannich‐type...Scheme 4.40 Organocatalyzed asymmetric Mannich‐type reaction of aldehydes wi...Scheme 4.41 syn‐Selective Mannich synthesis of propargylamines.Scheme 4.42 Asymmetric synthesis of syn‐propargylamines...Scheme 4.43 Synthesis of propargylamine via Friedel–Crafts‐type arylation.Scheme 4.44 Organocatalytic kinetic resolution of propargylamines. (a) Seide...Scheme 4.45 Organocatalytic reduction of alkynyl ketimines.Scheme 4.46 Synthesis of pyrroles from propargylamines.Scheme 4.47 Synthesis of pyrrolines from propargylamines.Scheme 4.48 Synthesis of pyridines from propargylamines.Scheme 4.49 Copper‐ and gold‐catalyzed synthesis of quinolines from propargy...Scheme 4.50 Synthesis of quinolines from N‐aryl‐propargylamines.Scheme 4.51 Synthesis of oxazoles from propargylamines.Scheme 4.52 Recent syntheses of oxazoles from propargylamides.Scheme 4.53 Reactions of propargylamine with CS₂.Scheme 4.54 Reactions of propargylamine with isothiocyanates.Scheme 4.55 Synthesis of thiazoline derivatives from N‐propargylamines using...

      5 Chapter 5Scheme 5.1 General equation for the reductive amination of an aldehyde or a ...Scheme 5.2 Reductive amination of 2‐methyl‐6‐ethyl‐aniline and methoxyaceton...Scheme 5.3 Reductive amination of the ketone function to produce the chiral ...Scheme 5.4 Chiral bisphosphine‐thiourea ligand (ZhaoPhos ligand).Scheme 5.5 Intramolecular asymmetric reductive amination using [Ir(COD)Cl]₂/...Scheme 5.6 Synthesis of (S)‐rivastigmine from meta‐hydroxyacetophenone and d...Scheme 5.7 Asymmetric reductive amination under dynamic kinetic resolution c...Scheme 5.8 Reductive amination of alkyl aryl ketones catalyzed by [Ru(OAc)₂]...Scheme 5.9 The Knölker iron catalyst and the TRIP Brønsted acid.Scheme 5.10 Asymmetric reductive amination of 2‐methyl cyclopentanone and cy...Scheme 5.11 Asymmetric hydroamination of an unactivated alkene with a second...Scheme 5.12 Enantioselective hydroamination of 1‐octene with 1‐tert‐butylimi...Scheme 5.13 Proposed mechanism for the asymmetric hydroamination of (R)‐3‐pe...Scheme 5.14 (a) Enantioselective hydroamination of styrene catalyzed by the ...Scheme 5.15 Iridium‐catalyzed hydroamination of norbornene by 4‐bromoaniline...Scheme 5.16 Intramolecular hydroaminomethylation of 5‐hex‐1‐ene amines catal...Scheme 5.17 Asymmetric intramolecular hydroamination of 2,2,5‐triphenylpent‐...Scheme 5.18 Stereoselective synthesis of 2,5‐substituted pyrrolidines from c...Scheme 5.19 Synthesis of the enantiopure α‐arylpyrrolid...Scheme 5.20 Chiral aziridine synthesis catalyzed by a Cu–H/(S)‐DTBM‐SegPhos ...Scheme 5.21 Hydroaminoalkylation of a secondary amine through C=C bond forma...Scheme 5.22 Synthesis of the tantalum catalyst precursor in the hydroaminoal...Scheme 5.23 Main steps of the catalytic cycle calculated by DFT, showing the...Scheme 5.24 Intermolecular coupling of N‐methylaniline with...Scheme 5.25 Hydroaminomethylation reaction of olefins: synthesis of amines....Scheme 5.26 Rh‐catalyzed hydroaminomethylation of styrene using L1–L4 ...Scheme 5.27 Energy values for the hydrogenation of E‐ and Z‐enamines.Scheme 5.28 Dynamic kinetic reductive amination of aldehydes developed by Li...Scheme 5.29 Rh‐ and organocatalyzed asymmetric hydroaminomethylation of styr...Scheme 5.30 Improved system in the metal and organocatalyzed asymmetric HAM ...Scheme 5.31 Rh‐catalyzed asymmetric interrupted hydroaminomethylation of sty...Scheme 5.32 Rh‐catalyzed asymmetric hydroaminomethylation of...Scheme 5.33 Rhodium species observed in the Rh‐catalyzed asymmetric hydroami...Scheme 5.34 Asymmetric photoredox β‐amination of α,...

      6 Chapter 6Scheme 6.1 Hajos–Parrish–Eder–Sauer–Wiechert reactions for the synthesis of ...Scheme 6.2 Alkylation of a substituted indanone 6 catalyzed by Cinchona alka...Scheme 6.3 Retrosynthetic approach for the synthesis of telcagepant.Scheme 6.4 Optimized organocatalytic asymmetric addition of nitromethane to ...Scheme 6.5 Retrosynthetic plan to obtain MK‐8613, by using asymmetric organo...Scheme 6.6 Enantioselective malonate addition to nitrostyrene 18 promoted by...Scheme 6.7 Retrosynthetic approach to funapide encompassing the organocataly...Scheme 6.8 Optimized enantioselective aldol reaction between 21 and formalde...Scheme 6.9 Retrosynthetic analysis of letermovir encompassing the key organo...Scheme 6.10 First‐generation enantioselective aza‐Michael cyclization based ...Scheme 6.11 Second‐generation enantioselective aza‐Michael cyclization based...Scheme 6.12 Possible transition states for the aza‐Michael reaction with H‐b...Scheme 6.13 Retrosynthetic approach for the synthesis of censavudine.Scheme 6.14 Synthesis of enantiopure pyranones 38 via a dynamic kinetic acyl...Scheme 6.15 Trapping of the furanose form 37′ with benzoic anhydride u...Scheme 6.16 Regio‐ and stereoselective (at P) introduction of the phosphoram...Scheme 6.17 Stereoselective phosphoramidate formation in uprifosbuvir synthe...Scheme 6.18 Pfizer manufacturing route to pregabalin encompassing an early‐s...Scheme 6.19 Retrosynthetic disconnections of the γ‐amino acid