Facile Synthesis of Oxime Amino Ethers via Lewis Acid Catalyzed S_N2-Type Ring Opening of Activated Aziridines with Aryl Aldehyde Oximes

Abstract

A simple strategy to access a wide range of substituted oxime amino ethers in good to high yields via Lewis acid catalyzed S_N2-type ring opening of activated aziridines with aryl aldehyde oximes is reported.

Key words

aziridine - oxime - oxime ether - Lewis acid catalyst - S_N2-type ring opening - stereoselectivity

• References and Notes

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• 26 Representative Experimental Procedure for the BF₃·OEt₂-Catalyzed Ring Opening of Aziridines with Aldehyde Oximes (Scheme 2) To a solution of the aziridine 1a–i (50 mg, 1.0 equiv) and 4-methoxybenzaldehyde oxime (2a, 1.5 equiv) in 2.0 mL dry dichloromethane was added anhydrous BF₃·OEt₂ (0.2 equiv) with a microsyringe at 0 °C under an argon atmosphere. The reaction mixture was stirred for an appropriate time (Scheme 2) at an appropriate temperature while the progress of the reaction was monitored by TLC. Upon completion the reaction was quenched with saturated aqueous NaHCO₃ solution. The aqueous layer was extracted with CH₂Cl₂ (3 × 5.0 mL) and it was washed with brine solution. The combined organic layers were dried over anhydrous Na₂SO₄, and the solvent was removed under reduced pressure. The crude concentrate was purified by flash column chromatography on silica gel (230–400 mesh) using 10% ethyl acetate in petroleum ether to provide the pure products 3a–i.(E)-N-(2-{[(4-methoxybenzylidene)amino]oxy}-2-phenylethyl)-4-methylbenzenesulfonamide (3a)The general method described above was followed when the aziridine 1a (50.0 mg, 0.1829 mmol, 1.0 equiv) was reacted with the 4-methoxybenzaldehyde oxime (2a, 41.5 mg, 0.274 mmol, 1.5 equiv) in the presence of BF₃·OEt₂ (4.6 μL, 0.037 mmol, 20 mol %) in dichloromethane (2.0 mL) at 0  °C to rt for 2 h to afford the product 3a (64.5 mg, 0.1518 mmol) as a white solid in 83 % yield ; mp 98–100  °C. R_f = 0.30 (EtOAc/petroleum ether, 3:7). IR (KBr): 3283, 2955, 2925, 2854, 1606, 1572, 1513, 1495, 1454, 1419, 1329, 1306, 1252, 1161, 1092, 1063, 1029, 955, 832, 814, 756, 701, 664, 602, 550 cm^{– 1}. ¹H NMR (500 MHz, CDCl₃): δ = 8.00 (s, 1 H), 7.71 (d, 2 H, J = 8.3 Hz), 7.42 (d, 2 H, J = 8.6 Hz), 7.33–7.23 (m, 7 H), 6.86 (d, 2 H, J = 8.6 Hz), 5.18 (dd, 1 H, J = 8.3, 3.9 Hz), 5.01–4.99 (m, 1 H), 3.82 (s, 3 H), 3.46–3.41 (m, 1 H), 3.37–3.32 (m, 1 H), 2.39 (s, 3 H). ¹³ C{¹ H} NMR (125 MHz, CDCl₃): δ = 161.3, 149.7, 143.5, 138.3, 137.0, 129.8, 128.7, 128.6, 128.3, 127.2, 126.7, 124.3, 114.2, 82.9, 55.4, 48.1, 29.8, 21.6. HRMS (ESI-TOF): m/z calcd for C₂₃H₂₅N₂O₄S [ M + H ]⁺: 425.1535; found: 425.1529