Published: Oct. 18, 2022
The present study reports an asymmetric organocascade reaction of oxindole-derived alkenes with 3-bromo-1-nitropropane efficiently catalyzed by the bifunctional catalyst. Spirooxindole-fused cyclopentanes were produced in moderate-to-good isolated yields (15-69%) excellent stereochemical outcomes. synthetic utility protocol was exemplified on a set additional transformations corresponding spirooxidondole compounds.
Language: Английский
Current Organic Chemistry, Journal Year: 2018, Volume and Issue: 23(1), P. 14 - 37
Published: Dec. 12, 2018
Hypervalent iodine reagents have been widely used in the construction of many important building blocks and privileged scaffolds bioactive natural products. This review article aims to briefly discuss strategies that hypervalent as oxidants synthesize spiroheterocyclic compounds stimulate further study for novel syntheses core structures using under metal-free conditions.
Language: Английский
Citations
19
Organic & Biomolecular Chemistry, Journal Year: 2019, Volume and Issue: 17(27), P. 6557 - 6561
Published: Jan. 1, 2019
The first organocatalytic enantioselective synthesis of dihydrofuran-spirooxindoles having a linkage at the 2-position dihydrofuran motif has been developed. Dioxindoles and benzylidene malononitriles were employed in this method. desired spirooxindole products obtained via Michael reaction followed by Pinner isomerization good to high yields with moderate diastereo enantioselectivities observed.
Language: Английский
Citations
17
Organic & Biomolecular Chemistry, Journal Year: 2018, Volume and Issue: 16(44), P. 8486 - 8490
Published: Jan. 1, 2018
Reacting Wittig reagents and the hypervalent iodine reagent iodosotoluene, in presence of 10 mol% Cu(tfacac)2 5 equiv. alkene, results a novel cyclopropanation reaction. The combination is believed to generate transient monocarbonyl iodonium ylide (MCIY) situ, which can be intercepted by copper catalyst give metallocarbene. Both ester ketone derived phosphoranes used, as styrenyl non-styrenyl alkenes, provides cyclopropanes yields up 81%.
Language: Английский
Citations
14
Asian Journal of Organic Chemistry, Journal Year: 2018, Volume and Issue: 7(10), P. 2065 - 2068
Published: Sept. 11, 2018
Abstract Catalyst and solvent‐free reactions have attracted great attention from chemists because of their inherent advantages that coincide with the principles sustainable chemistry increasing public awareness environmental protection. Here, we disclose first catalyst‐free intermolecular cyclopropanation phenyliodonium ylides electron‐deficient alkenes. Full conversion can be achieved at ambient temperature, in absence any catalyst, within a short reaction time. Importantly, such work reasonably well water or even under conditions, which enables green, convenient efficient way to synthesize valuable multifunctional vinylcyclopropanes.
Language: Английский
Citations
10
Angewandte Chemie, Journal Year: 2019, Volume and Issue: 131(47), P. 17115 - 17121
Published: Sept. 5, 2019
Abstract A facile and highly chemoselective synthesis of doubly activated cyclopropanes is reported where mixtures alkenes β‐dicarbonyl‐derived iodonium ylides are irradiated with light from blue LEDs. This metal‐free gives in yields up to 96 %, operative cyclic acyclic ylides, proceeds a variety electronically‐diverse alkenes. Computational analysis explains the high selectivity observed, which derives exclusive HOMO LUMO excitation, instead free carbene generation. The procedure operationally simple, uses no photocatalyst, provides access one step important building blocks for complex molecule synthesis.
Language: Английский
Citations
10
Synthesis, Journal Year: 2023, Volume and Issue: 55(20), P. 3281 - 3288
Published: June 22, 2023
Abstract An efficient diastereoselective synthesis of 1′,4′-dihydro-2′H-spiro[indoline-3,3′-quinolin]-2-one derivatives was achieved using catalytic amount l-proline. The key reactions involved in the present tandem reaction are aza-Michael addition and aldol reaction. This atom economic proceeded under mild conditions with a broad substrate scope excellent diastereoselectivity good to yields.
Language: Английский
Citations
3
Bulletin of the Korean Chemical Society, Journal Year: 2021, Volume and Issue: 42(2), P. 258 - 261
Published: Jan. 4, 2021
A novel and facile methodology for synthesizing diverse dihydrodibenzofuranones from easily accessible cyclic iodonium ylides is achieved. This protocol proceeds through the aryl migration of ylide followed by Pd‐catalyzed intramolecular arylation.
Language: Английский
Citations
5
Tetrahedron, Journal Year: 2020, Volume and Issue: 79, P. 131859 - 131859
Published: Dec. 9, 2020
Language: Английский
Citations
4
Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(15), P. 3283 - 3289
Published: June 6, 2024
Abstract Herein, we report a mild method for the synthesis of oxaspirocyclohexadienones by using combination Lewis acid‐HFIP mediated [2+3]‐annulation p ‐quinone methides ( p‐ QMs) and iodonium ylides. The proposed mechanism proceeds through one‐pot sequence carbonyl activation/cyclopropyl formation/Cloke‐Wilson rearrangement to provide broad range in moderate high yields. Interestingly, spiro‐annulated products were further converted tetrahydroxanthane derivatives via BF 3 .OEt 2 dienone‐phenol pathway. Moreover, also showed anti‐tuberculosis activity against Mycobacterium tuberculosis H37Ra ATCC25177.
Language: Английский
Citations
0
Asian Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 11(8)
Published: June 23, 2022
Abstract An organocatalytic enantioselective synthesis of dihydrofuran‐spirooxindoles has been developed. Dioxindoles and trans ‐α‐cyano‐α,β‐unsaturated ketones were engaged as the reaction partners in this method. The desired products obtained via bifunctional squaramide catalyzed Michael followed by Pinner isomerization.
Language: Английский
Citations
2