Advances in catalysis, Journal Year: 2023, Volume and Issue: unknown, P. 143 - 210
Published: Jan. 1, 2023
Language: Английский
Advances in catalysis, Journal Year: 2023, Volume and Issue: unknown, P. 143 - 210
Published: Jan. 1, 2023
Language: Английский
Organic Letters, Journal Year: 2021, Volume and Issue: 23(14), P. 5394 - 5399
Published: July 1, 2021
A fluorinative Beckmann fragmentation of α-oximinoamides was devised to provide synthetically useful carbamoyl fluorides. High selectivity for over a potentially competing rearrangement observed. This protocol has distinct mechanism and thus different substrate scope compared with other synthetic methods. α-Oximinoamides derived from the readily available secondary amines, lactams, or isatins were converted into structurally diverse
Language: Английский
Citations
39The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(12), P. 8158 - 8169
Published: June 8, 2022
The additive-free [3 + 2] annulation from isatins, amino acids with 2-styrylbenzoxazoles, was described, providing a series of functional and structurally complex 3,3'-pyrrolidinyl-spirooxindole derivatives containing four contiguous two quaternary stereogenic centers in high yields (up to 95%) excellent diastereoselectivities >25:1 dr). Interestingly, the reaction exhibits switchable regioselectivity depending on substrate acids. With proline or thioproline as substrate, afforded α-regioselective spirooxindole skeletons. In contrast, when piperidine acid is provided γ-regioselective
Language: Английский
Citations
15Beilstein Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 19, P. 1234 - 1242
Published: Aug. 22, 2023
A convenient synthetic procedure for the construction of novel dispirooxindole motifs was successfully developed by base-promoted three-component reaction ammonium acetate, isatins and in situ-generated 3-isatyl-1,4-dicarbonyl compounds. The piperidine-promoted dimedone adducts 3-ethoxycarbonylmethyleneoxindoles afforded mutlifunctionalized dispiro[indoline-3,2'-quinoline-3',3''-indoline] derivatives good yields with high diastereoselectivity. On other hand, a similar 3-phenacylideneoxindoles unique dispiro[indoline-3,2'-pyrrole-3',3''-indoline] cyclohexanedione substituent. plausible mechanism is proposed to explain formation different spirooxindoles.
Language: Английский
Citations
9Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 60(39), P. 21256 - 21260
Published: July 8, 2021
Dynamic kinetic asymmetric transformation (DYKAT) reactions of racemic diastereomer mixtures that afford the products as essentially single diastereomers with high enantioselectivities are described. We demonstrated DYKAT in diastereo- and enantioselective synthesis spirooxindoles bearing furan-fused rings. The starting materials DYKAT, dihydrobenzofuranone derivatives, were synthesized mixtures, these transformed to spirooxindole derivatives yields through Michael-Henry cascade nitrostyrenes under organocatalytic conditions. In reactions, regardless stereochemistry materials, all four isomers enantioselectivities, new chiral centers created.
Language: Английский
Citations
18The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(9), P. 5254 - 5274
Published: April 21, 2023
The first diastereo- and enantiodivergent asymmetric synthesis of new bis-spirocyclopropyloxindole scaffolds has been accomplished from the readily available isatin as a single starting material. Four rel-(1R,2R,3R), rel-(1S,2S,3R), rel-(1R,2R,3S), rel-(1S,2S,3S) configurations desired products were constructed in excellent enantiopurity via simple switch substrates using chiral auxiliary-controlled method. absolute configuration cycloadducts with three contiguous quaternary/tertiary stereogenic centers was confirmed through X-ray diffraction analysis. A facile versatile precursor 3-chlorooxindoles also introduced.
Language: Английский
Citations
4European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(15)
Published: Feb. 24, 2023
Abstract An enantioselective desymmetrization of curcumins with 3‐olefinic oxindoles involving a cascade double‐Michael addition strategy provides direct access to spirocyclohexanone‐oxindoles complete regio‐ and diastereoselectivities excellent enantioselectivities, besides good yields. The products possess three contiguous chiral centers multiple reactive functionalities. observed selectivities were rationalized by transitions state energy calculations at B3LYP//6‐31g(d) level DFT.
Language: Английский
Citations
3Chemistry - An Asian Journal, Journal Year: 2021, Volume and Issue: 16(17), P. 2435 - 2438
Published: Aug. 1, 2021
Abstract The unexpected gold‐catalyzed formal [3+2]‐cycloaddition of N ‐2,2,2‐trifluoroethylisatin ketimines with 2‐(1‐Alkynyl)‐2‐alken‐1‐ones is reported. Both diastereomers the corresponding cycloadducts were formed in moderate to excellent yields diastereoselectivities by switching catalytic system from mono‐gold gold/silver bimetallic system. practicality this protocol demonstrated scale‐up reaction and transformations cycloadduct.
Language: Английский
Citations
7ChemistrySelect, Journal Year: 2023, Volume and Issue: 8(37)
Published: Oct. 2, 2023
Abstract A convenient synthetic protocol for the construction of spiro[indoline‐3,3′‐quinoline]‐2,5′‐dione motifs was successfully developed by base promoted one‐pot three‐component reaction. In presence piperidine, reaction ammonium acetate, aromatic aldehydes and in situ generated 3‐isatyl 1,4‐dicarbonyl compounds, which were derived from mediated addition dimedone to 3‐methyleneoxindoles, resulted two diastereoisomers derivatives good yields with diastereoselectivity. The stereochemistry clearly elucidated isolation diastereomers determination several single crystal structures.
Language: Английский
Citations
2Angewandte Chemie, Journal Year: 2021, Volume and Issue: 133(39), P. 21426 - 21430
Published: July 8, 2021
Abstract Dynamic kinetic asymmetric transformation (DYKAT) reactions of racemic diastereomer mixtures that afford the products as essentially single diastereomers with high enantioselectivities are described. We demonstrated DYKAT in diastereo‐ and enantioselective synthesis spirooxindoles bearing furan‐fused rings. The starting materials DYKAT, dihydrobenzofuranone derivatives, were synthesized mixtures, these transformed to spirooxindole derivatives yields through Michael–Henry cascade nitrostyrenes under organocatalytic conditions. In reactions, regardless stereochemistry materials, all four isomers enantioselectivities, new chiral centers created.
Language: Английский
Citations
4Advances in catalysis, Journal Year: 2023, Volume and Issue: unknown, P. 143 - 210
Published: Jan. 1, 2023
Language: Английский
Citations
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