Role reversal in the cyclocondensation of cyclopentadiene with heterodienophiles derived from aryl amines and aldehydes: synthesis of novel tetrahydroquinolines
TL;DR: In this paper, it was shown that mononium ions derived from aryl amines and aldehydes function as heterodienophiles in the presence of cyclopentadiene giving rise to novel tetrahydroquinolines.
About: This article is published in Tetrahedron Letters.The article was published on 1988-01-01. It has received 164 citations till now. The article focuses on the topics: Cyclopentadiene & Aryl.
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1,801 citations
TL;DR: The main findings are: Lanthanide(II) Triflates in Organic Synthesis inorganic Synthesis 2295 10.2.1.
Abstract: 2.1.8. Michael Reaction 2245 2.1.9. Others 2247 2.2. Cyclization Reactions 2248 2.2.1. Carbon Diels−Alder Reactions 2248 2.2.2. Aza-Diels−Alder Reactions 2252 2.2.3. Other Hetero-Diels−Alder Reactions 2255 2.2.4. Ionic Diels−Alder Reaction 2256 2.2.5. 1,3-Dipolar Cycloadditions 2256 2.2.6. Other Cycloaddition Reactions 2258 2.2.7. Prins-type Cyclization 2259 2.3. Friedel−Crafts Acylation and Alkylation 2259 2.4. Baylis−Hillman Reaction 2263 2.5. Radical Addition 2264 2.6. Heterocycle Synthesis 2267 2.7. Diazocarbonyl Insertion 2270 3. C−X (X ) N, O, P, Etc.) Bond Formation 2271 3.1. Aromatic Nitration and Sulfonylation 2271 3.2. Michael Reaction 2272 3.3. Glycosylation 2273 3.4. Aziridination 2275 3.5. Diazocarbonyl Insertion 2276 3.6. Ring-Opening Reactions 2277 3.7. Other C−X Bond Formations 2280 4. Oxidation and Reduction 2280 4.1. Oxidation 2280 4.2. Reduction 2281 5. Rearrangement 2283 6. Protection and Deprotection 2285 6.1. Protection 2285 6.2. Deprotection 2288 7. Polymerization 2291 8. Miscellaneous Reactions 2291 9. Lanthanide(II) Triflates in Organic Synthesis 2295 10. Conclusion 2295 11. Acknowledgment 2295 12. References 2295
923 citations
TL;DR: In this paper, a review is devoted to the development in Povarov reaction and focuses on new efficient approaches based on this reaction to construct simple substituted (tetrahydro)quinolines and diverse N -polyheterocycles, including some alkaloids, which contain pyrroloquinoline or cyclopentaquinoline ring systems.
445 citations
TL;DR: Sc(OTf)3 is a new type of a Lewis acid that is different from typical Lewis acids such as AlCl3, BF3, SnCl4, etc as discussed by the authors.
359 citations
TL;DR: The three-component Povarov reaction of aldehydes, anilines, and benzyl N-vinylcarbamate 4 in the presence of 0.1 equiv of chiral phosphoric acid afforded cis-2,4-disubstituted tetrahydroquinolines in good yields and excellent enantiomeric excesses.
Abstract: The three-component Povarov reaction of aldehydes (2), anilines (3), and benzyl N-vinylcarbamate 4 in the presence of 01 equiv of chiral phosphoric acid 5 afforded cis-2,4-disubstituted tetrahydroquinolines (1) in good yields and excellent enantiomeric excesses The shortest synthesis of torcetrapib reported to date, which features this key three-component reaction, is documented
324 citations
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TL;DR: Cycloadditions de sels d'iminium obtenus par reaction de Mannich d'amines primaires avec des composes dieniques conjugues: obtention de tetrahydropyridines, d'aza-2bicyclo [2.2.1], heptenes-5; application a la synthese d'hexahydro indolizines et quinolizine par cycloaddition intramoleculaire des alcadienylamines correspondantes and a la
Abstract: Cycloadditions de sels d'iminium obtenus par reaction de Mannich d'amines primaires avec des composes dieniques conjugues: obtention de tetrahydropyridines, d'aza-2bicyclo [2.2.2] octenes-5, d'aza-2bicyclo [2.2.1], heptenes-5; application a la synthese d'hexahydro indolizines et quinolizines par cycloaddition intramoleculaire des alcadienylamines correspondantes et a la synthese de benzyl-1 methyl-2 octahydro quinoleine a partir de benzylamine et de decadiene-6,8al
245 citations
53 citations