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This Reprint Book highlights and overviews the most important and novel aspects of chiral auxiliary and chirogenesis in different natural/physical sciences and in modern technologies. In particular, some newly emerging classes of molecules used for these purposes are described. This book consists of four review articles and one research paper and is of interest for general chemistry readership, including graduate and postgraduate students, and for researchers specializing in the fields of chirality and stereochemistry

Research & information: general --- buckybowl --- corannulene --- sumanene --- bowl chirality --- bowl inversion --- asymmetric synthesis --- chiral resolution --- helicene --- chiral auxiliaries --- supramolecular chirogenesis --- chirality --- mechanical chirality --- mecanostereochemistery --- supramolecular chirality --- rotaxane --- aminolysis --- heterocycle --- receptors --- enantioselective recognition --- hydrogen bonding --- conformational rigidity --- configuration --- diastereomeric interactions --- macrocycle size --- pyridine --- dipolar interactions --- cucurbiturils --- hemicucurbiturils --- symmetry breaking --- helixes

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The Special Issue “Molecules from Side Reactions” is a collection of papers reporting on the synthesis and characterization of the molecules that come from unexpected synthetic routes. This is the first example of a Special Issue based on such a topic, notwithstanding that all synthetic chemists have isolated a side product during a chemical reaction. Instead of continuing to store the side products in the freezer, I have thought to give them the dignity of publication, making them available to the scientific community. The short manuscripts collected here respect the principle of “one compound per paper” and have the purpose of preserving the molecular diversity deriving from a chemical reaction. The molecular scaffolds are unexpected and intriguing, and could be useful starting points or intermediates for exploring novel reactions.

History of engineering & technology --- oxazole --- furan --- RORC reaction --- (E,Z)-isomerization --- nitration --- azaheterocycles --- N–C bond cleavage --- pyridine-imidazolium --- ribose --- psicose --- ketose --- rare sugar --- hydroxy methylation --- AICAR --- acadesine --- phosphorylation --- fluorination --- fluorinated nucleosides --- nucleoside analogues --- modified nucleosides --- chlorinated nucleosides --- AMPK --- organic synthesis --- bidentate directing groups --- benzamides --- chelation assistance --- bis-chelates --- C–H bond functionalization --- X-ray structure determination --- N′-acetylhydrazide --- 3-acetyl-2,3-dihydro-1,3,4-oxadiazole --- 1H-pyrazolo[3,4-b]pyridine --- heterocycle --- oxetane --- epoxide --- rearrangement --- carbohydrate --- C-glycosylation --- spiro-oxetane --- ester group migration --- glycosyl sulfoxide --- uronate --- thioglycoside oxidation --- mannose --- 8-Fluoro-2′-deoxyguanosine --- 19F NMR spectroscopy --- solid phase synthesis --- phosphoramidite --- muraymycins --- caprazamycins --- nucleosides --- uridine --- cyclization --- seven-membered rings --- conjugated diyne --- LAH reduction --- diacetal --- pent-1,2,3,4-tetraene intermediate --- ligand --- pyridine derivatives --- allenic compounds --- N-alkylation --- copper --- cyanide --- network --- guanidinium --- unexpected iminium cation --- n/a --- N-C bond cleavage --- C-H bond functionalization --- N'-acetylhydrazide --- 8-Fluoro-2'-deoxyguanosine

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The Special Issue “Molecules from Side Reactions” is a collection of papers reporting on the synthesis and characterization of the molecules that come from unexpected synthetic routes. This is the first example of a Special Issue based on such a topic, notwithstanding that all synthetic chemists have isolated a side product during a chemical reaction. Instead of continuing to store the side products in the freezer, I have thought to give them the dignity of publication, making them available to the scientific community. The short manuscripts collected here respect the principle of “one compound per paper” and have the purpose of preserving the molecular diversity deriving from a chemical reaction. The molecular scaffolds are unexpected and intriguing, and could be useful starting points or intermediates for exploring novel reactions.

History of engineering & technology --- oxazole --- furan --- RORC reaction --- (E,Z)-isomerization --- nitration --- azaheterocycles --- N-C bond cleavage --- pyridine-imidazolium --- ribose --- psicose --- ketose --- rare sugar --- hydroxy methylation --- AICAR --- acadesine --- phosphorylation --- fluorination --- fluorinated nucleosides --- nucleoside analogues --- modified nucleosides --- chlorinated nucleosides --- AMPK --- organic synthesis --- bidentate directing groups --- benzamides --- chelation assistance --- bis-chelates --- C-H bond functionalization --- X-ray structure determination --- N'-acetylhydrazide --- 3-acetyl-2,3-dihydro-1,3,4-oxadiazole --- 1H-pyrazolo[3,4-b]pyridine --- heterocycle --- oxetane --- epoxide --- rearrangement --- carbohydrate --- C-glycosylation --- spiro-oxetane --- ester group migration --- glycosyl sulfoxide --- uronate --- thioglycoside oxidation --- mannose --- 8-Fluoro-2'-deoxyguanosine --- 19F NMR spectroscopy --- solid phase synthesis --- phosphoramidite --- muraymycins --- caprazamycins --- nucleosides --- uridine --- cyclization --- seven-membered rings --- conjugated diyne --- LAH reduction --- diacetal --- pent-1,2,3,4-tetraene intermediate --- ligand --- pyridine derivatives --- allenic compounds --- N-alkylation --- copper --- cyanide --- network --- guanidinium --- unexpected iminium cation --- oxazole --- furan --- RORC reaction --- (E,Z)-isomerization --- nitration --- azaheterocycles --- N-C bond cleavage --- pyridine-imidazolium --- ribose --- psicose --- ketose --- rare sugar --- hydroxy methylation --- AICAR --- acadesine --- phosphorylation --- fluorination --- fluorinated nucleosides --- nucleoside analogues --- modified nucleosides --- chlorinated nucleosides --- AMPK --- organic synthesis --- bidentate directing groups --- benzamides --- chelation assistance --- bis-chelates --- C-H bond functionalization --- X-ray structure determination --- N'-acetylhydrazide --- 3-acetyl-2,3-dihydro-1,3,4-oxadiazole --- 1H-pyrazolo[3,4-b]pyridine --- heterocycle --- oxetane --- epoxide --- rearrangement --- carbohydrate --- C-glycosylation --- spiro-oxetane --- ester group migration --- glycosyl sulfoxide --- uronate --- thioglycoside oxidation --- mannose --- 8-Fluoro-2'-deoxyguanosine --- 19F NMR spectroscopy --- solid phase synthesis --- phosphoramidite --- muraymycins --- caprazamycins --- nucleosides --- uridine --- cyclization --- seven-membered rings --- conjugated diyne --- LAH reduction --- diacetal --- pent-1,2,3,4-tetraene intermediate --- ligand --- pyridine derivatives --- allenic compounds --- N-alkylation --- copper --- cyanide --- network --- guanidinium --- unexpected iminium cation

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A total of 16 original research articles. Contributions from 10 countries from 3 continents. Organic synthesis towards novel heterocyclic compounds. Fully characterized inorganic and organic molecules including X-ray crystallographic analysis. Cyclization reactions, reactivity of aromatic compounds and improved synthetic methodologies of important intermediate compounds.

heterocycle --- piperazine --- pyrimidine --- DABCO --- nucleophilic displacement --- chlorination --- [1,3]-H shift --- aza-Michael addition --- DFT calculations --- dimethyl acetylenedicarboxylate --- isoxazolo[3,4-b]quinolin-3(1H)-one --- pyrazolines --- curcuminoids --- nitrogen heterocycles --- cytotoxic --- DNA binding --- MDR reversal --- oxygen-nitrogen heterocycles --- 11a,12-dihydrobenzo[b]benzo[5,6][1,4]oxazino[2,3-e][1,4]oxazine --- disulfur dichloride --- o-aminophenol --- condensation --- 4-anilino-quin(az)olines --- hinge binder --- conformational flexibility --- kinase inhibitor design --- imine --- Schiff base --- X-ray crystallographic analysis --- Cu(II) complex --- gamma-amino acid --- ruthenium --- carbonyl complex --- azopyridine --- anion radical --- electronic structure --- magnetic properties --- chalcogenophene --- heterocycles --- ligands --- pyridine derivatives --- thiophene derivatives --- aminocyclopentitol --- bicyclic aziridine --- water chemistry --- nucleophilic substitution --- homopiperazine --- X-ray structure --- C–C bond length --- 15N-NMR --- catechol --- alkyne --- thiol-alkyne click reaction --- domino reactions --- bromination --- intramolecular SN displacement --- carbocyclic hydantoins --- N-1 substituted hydantoin --- spiro hydantoins --- imidazolidine-2,4-diones --- stereochemistry --- NMR --- HRMS --- GIAO --- ring closing --- Au-nanoparticles --- NaBH4 --- amino-substituted fused oxazolocoumarin --- fused oxazolocoumarins --- chemoselective reduction --- o-hydroxynitrocoumarins --- benzimidazole --- nucleophilic aromatic substitution --- thiosemicarbazone --- n/a --- C-C bond length