A Novel Synthesis of Aryl α-Imino Esters from Aryl Diazoacetate

Abstract

Aryl α-imino esters were synthesized from the reaction of aryl diazoacetate with arylamine in the presence of diethyl azodicarboxylate (DEAD) catalyzed by dirhodium acetate. The α-imino esters were formed through fragmentation of corresponding aminals.

Key words

α-imino ester - dirhodium(II) acetate - α-diazoacetate - ammonium ylide - aminal

References

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• 17 Typical Procedure. To a refluxing CH₂Cl₂ (8 mL) solution of Rh_{2 (}OAc)₄ (2.1 mg, 1 mol%), p-nitroaniline 2c (66.6 mg, 0.48 mmol) and DEAD (83.5 µL, 0.53 mmol) under argon atmosphere was added phenyldiazoacetate 1a (85 mg, 0.48 mmol) in 4 mL of CH₂Cl₂ over 1 h via a syringe pump. After completing the addition, the reaction mixture was cooled to r.t. and the solvent was removed. The crude product was purified by flash chromatography on silica gel by using 1% EtOAc-light petroleum as eluent to give a yellow solid 3c, yield 60%. Single crystal 3c was grown in hexane and EtOAc solution: mp 93.1-94.1 °C. ¹H NMR (300 MHz, CDCl₃): δ = 8.24 (d, J = 8.9 Hz, 2 H), 7.88 (m, 2 H), 7.48-7.61 (m, 3 H), 7.04 (d, J = 8.9 Hz, 2 H), 3.67 (s, 3 H). ¹³C NMR (75 MHz, CDCl₃): δ = 174.4, 164.3, 161.2, 156.0, 144.9, 132.8, 129.1, 128.5, 124.9, 120.0, 52.3. MS (EI, 70 eV): m/z (rel. intensity) = 284 (12) [M⁺], 225 (84), 179 (41), 167 (8), 76 (100), 59 (40). Anal. Calcd for C₁₅H₁₂N₂O₄: C, 63.38; H, 4.25; N, 9.85. Found: C, 63.12; H, 4.29; N, 9.85