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

Haoxi Huang; Yuanhua Wang; Zhiyong Chen; Wen H. Hu

doi:10.1055/s-2005-872689

LETTER

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

Haoxi Huang^a,^b, Yuanhua Wang^a, Zhiyong Chen^a, Wen H. Hu*^a
^a Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province and Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, P. R. of China
Fax: +86(28)85229250; e-Mail: huwh@cioc.ac.cn;
^b Graduate School of the Chinese Academy of Sciences, Beijing, P. R. of China

Abstract

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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

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References

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15a Crystal data for 3c: C₁₅H₁₂N₂O₄, MW = 284.27, space group P21/n, a = 11.0730 (10) Å, b = 7.6470 (10) Å, c = 16.643 (2) Å, V = 1388.7 (3) Å³, Z = 4, ρ_calcd = 1.360 Mg/m³, F(000) = 592, λ = 0.71073 Å, T = 290 (2)K, µ(Mo-K_α) = 0.101 mm^-1. Data for the structure were collected on a Siemens P-4X four-circle diffractometer. Intensity measurements were performed on a crystal (dimensions 0.62 × 0.40 × 0.40 mm) in the range 4.12 < 2θ < 50.10°. Of the 2740 measured reflections, 2591were independent (R _int = 0.2941). The structure was solved by direct methods (SHELXS-97) and refined by full-matrix least squares on F ². The final refinements converged at R1 = 0.0360 for I > 2σ(I), wR2 = 0.0796 for all data. The final difference Fourier synthesis gave a min/max residual electron density of 0.134 and -0.115eÅ^-3

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17 Typical Procedure. To a refluxing CH₂Cl₂ (8 mL) solution of Rh₂ ₍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