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

<A NAME="RU23305ST-1A">1a</A> Weinreb SM. Top. Curr. Chem. 1997, 190: 131

<A NAME="RU23305ST-1B">1b</A> Borzilleri RM. Weinreb SM. Synthesis 1995, 347

<A NAME="RU23305ST-1C">1c</A> Mikami K. Yajima T. Kaneko M. Amino Acids 1998, 14: 311

<A NAME="RU23305ST-1D">1d</A> Mikami K. Kaneko M. Yajima TS. Tetrahedron Lett. 1993, 34: 4841

<A NAME="RU23305ST-2A">2a</A> Yao S. Fang X. Jørgensen KA. Chem. Commun. 1998, 2547

<A NAME="RU23305ST-2B">2b</A> Drury WJIII. Ferraris D. Cox C. Young B. Lectka T. J. Am. Chem. Soc. 1998, 120: 11006

<A NAME="RU23305ST-3A">3a</A> Yao S. Johannsen M. Hazell RG. Jørgensen KA. Angew. Chem. Int. Ed. 1998, 37: 3121 ; Angew. Chem. 1998, 110, 3318

<A NAME="RU23305ST-3B">3b</A> Jørgensen KA. Angew. Chem. Int. Ed. 2000, 39: 3558 ; Angew. Chem. 2000, 112, 3702

<A NAME="RU23305ST-3C">3c</A> Yao S. Saaby S. Hazell RG. Jørgensen KA. Chem.-Eur. J. 2000, 2435

<A NAME="RU23305ST-4A">4a</A> Yamamoto Y. Nishii S. Maruyama K. Komatsu T. Ito W. J. Am. Chem. Soc. 1986, 108: 7778

<A NAME="RU23305ST-4B">4b</A> Fang X. Johannson M. Yao S. Gathergood N. Hazell R. Jørgensen KA. J. Org. Chem. 1999, 64: 4844

<A NAME="RU23305ST-4C">4c</A> Ferraris D. Young B. Dudding T. Lectka T. J. Am. Chem. Soc. 1998, 120: 4548

<A NAME="RU23305ST-4D">4d</A> Ferraris D. Young B. Cox C. Dudding T. Drury WJ. Lev R. Taggi AE. Lectka T. J. Am. Chem. Soc. 2002, 124: 67

<A NAME="RU23305ST-5A">5a</A> Juhl K. Gathergood N. Jørgensen KA. Angew. Chem. Int. Ed. 2001, 40: 2995 ; Angew. Chem. 2001, 113, 3083

<A NAME="RU23305ST-5B">5b</A> Marigo M. Kjaersgaard A. Juhl K. Gathergood N. Jørgensen KA. Chem.-Eur. J. 2003, 9: 2359

<A NAME="RU23305ST-5C">5c</A> Bernardi L. Gothelf AS. Hazell RG. Jorgensen KA. J. Org. Chem. 2003, 68: 2583

<A NAME="RU23305ST-5D">5d</A> Kobayashi S. Matsubara R. Nakamura Y. Kitagawa H. Sugiura M. J. Am. Chem. Soc. 2003, 125: 2507

<A NAME="RU23305ST-6A">6a</A> Saaby S. Fang X. Gathergood N. Jørgensen KA. Angew. Chem. Int. Ed. 2000, 39: 4114 ; Angew. Chem. 2000, 112, 4280

<A NAME="RU23305ST-6B">6b</A> Hao J. Taktak S. Aikawa K. Yusa Y. Hatano M. Mikami K. Synlett 2001, 1443

<A NAME="RU23305ST-7A">7a</A> Juhl K. Hazell R. Jørgensen KA. J. Chem. Soc., Perkin Trans. 1 1999, 2293

<A NAME="RU23305ST-7B">7b</A> Aggarwal VK. Alonso E. Ferrara M. Spey SE. J. Org. Chem. 2002, 67: 2335

<A NAME="RU23305ST-7C">7c</A> Aggarwal VK. Ferrara M. Org. Lett. 2000, 2: 4107

<A NAME="RU23305ST-8A">8a</A> Wack H. Drury WJ. Taggi AE. Ferraris D. Lectka T. Org. Lett. 1999, 1: 1985

<A NAME="RU23305ST-8B">8b</A> Taggi AE. Hafez AM. Wack H. Young B. Drury WJ. Lectka T. J. Am. Chem. Soc. 2000, 122: 7831

<A NAME="RU23305ST-8C">8c</A> France S. Wack H. Hafez AM. Taggi AE. Witsil DR. Lectka T. Org. Lett. 2002, 4: 1603

<A NAME="RU23305ST-8D">8d</A> Akiyama T. Daidouji K. Fubhibe K. Org. Lett. 2003, 5: 3691

<A NAME="RU23305ST-9A">9a</A> Taggi AE. Hafez AM. Wack H. Young B. Drury WJ. Lectka T. J. Am. Chem. Soc. 2000, 122: 7831

<A NAME="RU23305ST-9B">9b</A> Taggi AE. Hafez AM. Wack H. Young B. Ferraris D. Lectka T. J. Am. Chem. Soc. 2002, 124: 6626

<A NAME="RU23305ST-10A">10a</A> Aldea R. Alper H. J. Organomet. Chem. 2000, 594: 454

<A NAME="RU23305ST-10B">10b</A> Iwasaki F. Onomura O. Mishima K. Kanematsu T. Maki T. Matsumura Y. Tetrahedron Lett. 2001, 42: 2525

<A NAME="RU23305ST-10C">10c</A> Abe H. Amii H. Uneyama K. Org. Lett. 2001, 3: 313

<A NAME="RU23305ST-11A">11a</A> Saaby S. Nakama K. Lie MA. Hazell RG. Jørgensen KA. Chem.-Eur. J. 2003, 6145

<A NAME="RU23305ST-11B">11b</A> Stilz HU. Jablonka B. Just M. Knolle J. Paulus EF. Zoller G. J. Med. Chem. 1996, 39: 2118

<A NAME="RU23305ST-12A">12a</A> Hickmott PW. Tetrahedron 1982, 38: 1975

<A NAME="RU23305ST-12B">12b</A> Boeykens M. De Kimpe N. Tehrani KA. J. Org. Chem. 1994, 59: 6973

<A NAME="RU23305ST-12C">12c</A> Taguch K. Westheimer FH. J. Org. Chem. 1971, 36: 1570

Samples for the preparation of α-ketoesters, see:

<A NAME="RU23305ST-13A">13a</A> Tatlock JH. J. Org. Chem. 1995, 60: 6221

<A NAME="RU23305ST-13B">13b</A> Hon YS. Lin WC. Tetrahedron Lett. 1995, 36: 7693

<A NAME="RU23305ST-13C">13c</A> Babudti F. Fiandanese V. Marchese G. Punzi A. Tetrahedron 1996, 52: 13513

<A NAME="RU23305ST-13D">13d</A> Grison C. Coutrot F. Coutrot P. Tetrahedron 2001, 57: 6215

<A NAME="RU23305ST-13E">13e</A> Takahashi T. Okano T. Harada T. Imamura K. Yamada H. Synlett 1994, 121

<A NAME="RU23305ST-14A">14a</A> Paulissen R. Hayez E. Hubert A. Teyssie P. Tetrahedron Lett. 1974, 607

<A NAME="RU23305ST-14B">14b</A> Aller E. Buck RT. Drysdale MJ. Ferris L. Haigh D. Moody CJ. Pearson ND. Sanghera JB. J. Chem. Soc., Perkin Trans. 1 1996, 2879

<A NAME="RU23305ST-15A">15a</A> 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

<A NAME="RU23305ST-15B">15b</A> CCDC-238733 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: +44 (1223)336033; or deposit@ ccdc.cam.ac.uk]

<A NAME="RU23305ST-16A">16a</A> Wang YH. Zhu YX. Chen ZY. Mi A. Hu W. Doyle MP. Org. Lett. 2003, 5: 3923

<A NAME="RU23305ST-16B">16b</A> Huang HX. Wang YH. Chen ZY. Hu W. Adv. Synth. Catal. 2005, 347: 531

<A NAME="RU23305ST-17">17</A> 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