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Volumn , Issue 13, 2008, Pages 2041-2045

Trimethylsilyl trifluoromethanesulfonate mediated addition-cyclization of N-vinyloxazolidin-2-ones to nitrones: An efficient access to 4-substituted 5-azaisoxazolidines

(4) Nguyen, Thanh Binh a Martel, Arnaud a Dhal, Robert a Dujardin, Gilles a

a UNIVERSITÉ DU MAINE (France)

Author keywords

Cycloaddition; Dipolarophile; N alkenyloxazolidinone; Nitrone; Trimethylsilyl trifluoromethanesulfonate

Indexed keywords

5 AZAISOXAZOLIDINE DERIVATIVE; ISOXAZOLIDINE DERIVATIVE; N VINYLOXAZOLIDIN 2 ONE DERIVATIVE; NITRONE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; TRIMETHYLSILYL DERIVATIVE; TRIMETHYLSILYL TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; CYCLOADDITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 49749092381 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1077963 Document Type: Article

Times cited : (5)

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17
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- Under these conditions, the adducts between N- vinyloxazolidin-2-ones la,c and unactivated nitrone (R = aryl) could not be obtained due to low reactivity.
- Under these conditions, the adducts between N- vinyloxazolidin-2-ones la,c and unactivated nitrone (R = aryl) could not be obtained due to low reactivity.

18
- 49749132638
- Dipolarophiles 1a, 1b, Z)-1c, Z)-1d, E)-1c8 and (E)-1c16 were prepared according to literature reports. Procedure for the Preparation of (E)3-(4-Nitrosty-ryl) oxazolidin-2-one: A solution of (Z)-1d (2.34 g, 0.1 mol, and p-toluenesulfonic acid monohydrate (50 mg) in toluene (50 mL) was refluxed for 16 h. The solution was cooled to r.t, washed with sat. aq NaHCO3 (10 mL, and dried over MgSO4. The solvent was removed. The crude product was recrystallized (CH2Cl 2-n-pentane) to afford the product as a yellow solid (2.15 g, 92, mp 170-171 °C (Et2O, IR (neat, 1758, 1644, 1506, 1479, 1421, 1407, 1207, 1102, 1078 cm-1. 1H NMR (400 MHz, CDCl3, δ, 8.14-8.18 (m, 2 H, 7.56 (d, J, 14.7 Hz, 1 H, 7.42-7.46 (m, 2 H, 5.81 (d, J, 14.7 Hz, 1 H, 4.55-4.60 m, 2
- 4: 235.0719; found: 235.0718.

19
- 49749135933
- General Procedure for the Cycloaddition: At 0 °C, TMSOTf (222 mg, 1 mmol) was added dropwise to a mixture of nitrone 2 (1 mmol) and dipolarophile 1 (1 mmol) in chloroform (100 μL, The reaction mixture was allowed to warm to r.t, stirred for 16 h, then diluted with CH 2Cl2 (25 mL) and neutralized with sat. aq NaHCO 3 (10 mL, After drying (MgSO4, the solvent was removed and the crude product was purified by flash column chromatography on silica gel (cyclohexane-Et2O) to afford the corresponding adducts 4 and 3. Both diastereomers could be easily separated by conventional flash chromatography Rf,cis > Rf,trans, ΔRf 0.2; eluent: Et2O-cyclohexane, 1:1, In most cases, isolated yields of the more polar trans adduct suffered from partial loss during column chromatography purification. The results are presented i
- 3 (10 mL).

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