Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 123 - 173
Published: Jan. 1, 2024
Language: Английский
ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 4017 - 4024
Published: Feb. 20, 2025
Language: Английский
Citations
3
Accounts of Chemical Research, Journal Year: 2025, Volume and Issue: unknown
Published: Jan. 17, 2025
ConspectusThe Mannich reaction, involving the nucleophilic addition of an enol(ate) intermediate to imine or iminium ion, is one most widely used synthetic methods for synthesis β-amino carbonyl compounds. Nevertheless, homo-Mannich which utilizes a homoenolate as partner and provides straightforward access valuable γ-amino compounds, remains underexplored. This can be largely attributed difficulties in generation manipulation species, despite various equivalents that have been developed. Among developed, cyclopropanol stands out due its intriguing reactivities endowed by highly strained cyclopropane. Upon activation metal, cyclopropyl alcohol prone undergo endocyclic C(sp3)–C(sp3) bond cleavage give β-keto radical intermediate, sets stage diverse range transformations. account outlines our recent progress development reaction applications natural product total synthesis. new methodology classified into two subtypes: 1) with imines ions 2) homo-Mannich-type heteroarenes. Through different ways generate ions, tandem sequential reactions C–H oxidation/homo-Mannich, Bischler–Napieralski/homo-Mannich, asymmetric allylation/homo-Mannich leading rapid assembly core scaffolds sarpagine, koumine, ibophyllidine, Aspidosperma, Melodinus, Kopsia alkaloids. Besides ring-opening indole pyrrole rings deliver schizozygane indolizidine Based on these advancements, we accomplished 29 alkaloids belonging 8 families. In this Account, present complete picture works concerning design, method development, It anticipated methodologies will find broad realm
Language: Английский
Citations
1
Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(37)
Published: July 25, 2023
We report here a homo-Mannich reaction of cyclopropanol with an iminium ion, generated by asymmetric allylic dearomatization indole, to construct tricyclic hydrocarbazole core, which is shared variety monoterpenoid indole alkaloids across families. Through this approach, all-carbon quaternary stereogenic center as well allyl and ketone group were installed. Using functionalized the structural platform, D ring E rings different sizes (i.e., five-, six-, seven-membered) successively or simultaneously assembled, leading collective synthesis seven belonging ibophyllidine, Aspidosperma, Kopsia, Melodinus alkaloid
Language: Английский
Citations
15
ChemistrySelect, Journal Year: 2023, Volume and Issue: 8(32)
Published: Aug. 23, 2023
Abstract Cyclopropanols, due to their particular chemistry, can participate in various synthetic reactions with retention or cleavage of the strained three‐membered ring. Direct cross‐coupling ring‐opening reaction such molecules access organic compounds, as ketones has great importance medicinal chemistry and material sciences. Hence, coupling reaction/cyclization cyclopropanols for constructing new valuable presence a transition metal catalyst under metal‐free conditions is described this context. The features are discussed, mechanisms challenging highlighted.
Language: Английский
Citations
12
Organic Letters, Journal Year: 2024, Volume and Issue: 26(19), P. 4043 - 4048
Published: May 2, 2024
A radical ring-opening arylation of cyclopropanol with 1,2,3-triazole has been achieved. This synthetic protocol provides straightforward access to a wide range structurally diverse and chiral 4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyridines high efficiency from readily available cyclopropanols.
Language: Английский
Citations
3
Chemical Communications, Journal Year: 2024, Volume and Issue: unknown
Published: Jan. 1, 2024
Synthetic strategies towards pyrroles within chiral frameworks are summarised, focussing on reports published 2010–2023.
Language: Английский
Citations
2
Organic Letters, Journal Year: 2024, Volume and Issue: 26(33), P. 6950 - 6954
Published: July 9, 2024
Tricyclic 6-7-6 and 6-8-6 carbon ring systems are present in numerous biologically active natural molecules. However, simple efficient synthetic approaches to these scaffolds remain challenging. Herein, we report a versatile strategy for constructing via Fe(NO
Language: Английский
Citations
1
Organic Letters, Journal Year: 2024, Volume and Issue: 26(31), P. 6698 - 6702
Published: July 30, 2024
A gold-catalyzed cycloisomerization/nucleophilic addition/C–O rearrangement was developed starting from readily available pyrrole precursors. This efficient synthesis of 7,8-dihydroindolizin-6(5H)-ones (with the creation new C–C and C–O bonds) allows access to key intermediates for natural biologically active molecules. The functionalization process independently optimized both carbon oxygen nucleophiles, versatility this methodology established by 36 different derivatives (yields up 90%).
Language: Английский
Citations
1
Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(37)
Published: July 25, 2023
Abstract We report here a homo‐Mannich reaction of cyclopropanol with an iminium ion, generated by asymmetric allylic dearomatization indole, to construct tricyclic hydrocarbazole core, which is shared variety monoterpenoid indole alkaloids across families. Through this approach, all‐carbon quaternary stereogenic center as well allyl and ketone group were installed. Using functionalized the structural platform, D ring E rings different sizes (i.e., five‐, six‐, seven‐membered) successively or simultaneously assembled, leading collective synthesis seven belonging ibophyllidine, Aspidosperma, Kopsia , Melodinus alkaloid
Language: Английский
Citations
2
Elsevier eBooks, Journal Year: 2024, Volume and Issue: unknown
Published: Jan. 1, 2024
Citations
0