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Synlett 2015; 26(02): 238-242
DOI: 10.1055/s-0034-1379602
DOI: 10.1055/s-0034-1379602
letter
Synthesis of Isoxazolidine-Fused Eight-Membered Heterocycles via an Intramolecular Nitrone–Alkene Cycloaddition
Weitere Informationen
Publikationsverlauf
Received: 17. September 2014
Accepted after revision: 27. Oktober 2014
Publikationsdatum:
17. Dezember 2014 (online)
![](https://www.thieme-connect.de/media/synlett/201502/lookinside/thumbnails/10.1055-s-0034-1379602-1.jpg)
Abstract
An intramolecular nitrone–alkene cycloaddition yielded novel tricyclic eight-membered ring with a cis-fused isoxazolidine in good to excellent yields under mild reaction conditions.
Key words
1,3-dipolar cycloaddition - diastereoselectivity - fused-ring systems - eight-membered ring - isoxazolidineSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379602.
- Supporting Information
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References and Notes
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- 14 Typical Experimental Procedure for the Synthesis of 4Compound 1a (225 mg, 0.50 mmol) in CH2Cl2 (20 mL) was treated with DIPEA (0.697 mL, 4.0 mmol) and DMSO (0.709 mL, 10.0 mmol). The reaction mixture was cooled to 0–2 °C, and SO3–pyridine (320 mg, 2.0 mmol) was added in two portions. The resulting solution was stirred for 2 h at 0–2 °C. The reaction mixture was then diluted with CH2Cl2 (20 mL), washed with 0.2 M aq KHSO4 (20 mL), H2O (20 mL), and brine (20 mL). Then it was dried over MgSO4, filtered, and diluted with CH2Cl2 to give a solution of crude aldehyde 2a in CH2Cl2 (50 mL). To the above solution was added NaOAc (49 mg, 0.60 mmol) and N-methylhydroxylamine hydrochloride (49 mg, 0.60 mmol). The mixture was stirred for 2 h at 25 °C, then washed with sat. aq Na2CO3 (25 mL), dried over MgSO4, and concentrated in vacuo. Purification by flash chromatography (PE–EtOAc, 5:1 to 1:2 v/v) afforded the desired product 4a (193 mg, 81% yield); mp 153–154 °C. 1H NMR (300 MHz, CDCl3): δ = 8.34 (s, 1 H), 7.44–7.42 (m, 2 H), 7.40–7.30 (m, 5 H), 7.00–6.96 (m, 2 H), 5.51 (d, 1 H, J = 13.5 Hz), 4.41 (t, 2 H, J = 7.5 Hz), 3.98 (t, 1 H, J = 8.4 Hz), 3.85 (s, 3 H), 3.51 (dd, 1 H, J = 15.6, 9.3 Hz), 3.46 (ddd, 1 H, J = 9.3, 8.4, 6.3 Hz), 3.21–3.16 (m, 4 H), 2.18 (br, 1 H), 2.11 (s, 3 H). 13C NMR (75 MHz, CDCl3): δ = 170.9, 169.6, 160.9, 158.2, 155.8, 137.4, 137.2, 128.92, 128.87, 128.2, 118.0, 116.1, 115.0, 70.4, 66.5, 55.4, 54.7, 49.4, 49.3, 42.9, 34.8. ESI-MS: m/z = 478.2 [M + H+].
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