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Synlett 2022; 33(05): 468-472
DOI: 10.1055/a-1760-8951
DOI: 10.1055/a-1760-8951
letter
Hydrothiolation of Donor–Acceptor Cyclopropanes through Er(OTf)3-Promoted Three-Component Ring-Opening Reaction
We thank Alexander von Humboldt Foundation for the Linkage Research Group Program Award and Iran National Science Foundation for the research fellowship (Grant No. 99029802).
Abstract
A novel ring-opening reaction of donor–acceptor cyclopropanes (DACs) through a one-pot three-component nucleophilic addition of amines, CS2, and DACs has been described. New γ-dithiocarbamate dialkyl malonate skeletons were obtained in up to 97% yield.
Key words
donor–acceptor cyclopropanes - hydrothiolation - ring-opening reaction - three-component reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1760-8951.
- Supporting Information
Publikationsverlauf
Eingereicht: 19. Januar 2022
Angenommen nach Revision: 03. Februar 2022
Accepted Manuscript online:
04. Februar 2022
Artikel online veröffentlicht:
21. Februar 2022
© 2022. Thieme. All rights reserved
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- 12 Dithiocarbamates 4a–o: General ProcedureTo a mixture of carbon disulfide 2 (0.6 mmol, 2 equiv) and toluene (3 mL) as a solvent, amine 1a–f (0.3 mmol) was added, and the mixture was stirred for 30 min at ambient temperature. Then the donor–acceptor cyclopropane 3a–j (0.3 mmol) and Er(OTf)3 (18 mg, 10 mol%) as a Lewis acid was added, and the mixture was heated at 90 °C for 4 h. After completion, the solvent was removed in vacuo, and the products were purified by flash column chromatography using n-hexane/EtOAc (8:1) as an eluent to give dithiocarbamates 4a–o. Dimethyl 2-{2-phenyl-2-[(piperidine-1-carbonothioyl)-thio]ethyl}malonate (4a)Colorless solid; mp 130–131 °C (96 mg , yield 82%, silica gel, n-hexane/EtOAc = 8:1). 1H{13C} NMR (CDCl3, 300 MHz): δ = 7.41–7.28 (m, 5 H, HAr), 5.27 (dd, J = 8.6, 2.2 Hz, 1 H, SCH), 4.25 (br s, 2 H, NCHeq), 3.84 (br s, 2 H, NCHax), 3.78 (s, 3 H, OMe), 3.59 (s, 3 H, OMe), 3.44 (t, J = 7.3 Hz, 1 H, CH), 2.83–2.61 (m, 2 H, CH2), 1.60–1.70 (m, 6 H, 3(CH2)) ppm. 13C{1H} NMR (CDCl3, 75 MHz): δ = 193.5, 169.2, 169.1, 139.5, 128.7, 128.3, 127.8, 53.7, 52.7, 52.5, 50.0, 35.2, 25.9, 25.4, 24.2 ppm. HRMS-ESI: m/z calcd for C19H26NO4S2 [M + H]+: 396.1297; found: 396.1296.
- 13 CCDC 2130147 and 2130148 contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures.