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Enantioselective chlorination of β-keto esters and amides catalyzed by chiral copper(Ⅱ) complexes of squaramide-linked bisoxazoline ligand

Enantioselective chlorination of β-keto esters and amides catalyzed by chiral copper(Ⅱ) complexes of squaramide-linked bisoxazoline ligand
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摘要 Enantioselective chlorination of b-keto esters and amides catalyzed by squaramide-linked bisoxazoline ligand–Cu（OAc）2complexes was investigated. The corresponding chlorinated products were obtained in excellent yields with moderate enantioselectivities. The effect of solvent, temperature, Lewis acid, and ligand structure on the reaction is discussed. This was the first investigation of catalytic asymmetric achlorination of b-keto amides. This study has highlighted that a simple chiral squaramide–oxazoline with cheap Cu（OAc）2 H2 O complexes can catalyze this chlorination. Enantioselective chlorination of b-keto esters and amides catalyzed by squaramide-linked bisoxazoline ligand–Cu（OAc）2complexes was investigated. The corresponding chlorinated products were obtained in excellent yields with moderate enantioselectivities. The effect of solvent, temperature, Lewis acid, and ligand structure on the reaction is discussed. This was the first investigation of catalytic asymmetric achlorination of b-keto amides. This study has highlighted that a simple chiral squaramide–oxazoline with cheap Cu（OAc）2 H2 O complexes can catalyze this chlorination.
作者 Sheng-Jian Jia Da-Ming Du
机构地区 School of Chemical Engineering and Environment
出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2014年第11期1479-1484,共6页 中国化学快报（英文版）
基金 financial support from the National Natural Science Foundation of China(Nos.21072010 and 21272024)
关键词 Asymmetric catalysis Bisoxazoline Squaramide Chlorination b-Keto esters Asymmetric catalysis Bisoxazoline Squaramide Chlorination b-Keto esters
分类号 O641.4 [理学—物理化学]
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参考文献11

  • 1BinFU DaMingDU QingXIA.Convenient Synthesis of Bis(oxazoline) Dicarboxylate Derivatives.[J].Chinese Chemical Letters,2004,15(4):383-385. 被引量：1
  • 2Sheng-Jian Jia,Da-Ming Du.Enantioselective Friedel–Crafts alkylation of indoles with β,γ-unsaturated α-ketoesters catalyzed by new squaramide-linked bisoxazoline–Zn(OTf) 2 complexes[J].Tetrahedron: Asymmetry.2014
  • 3Jiahuan Peng,Da‐Ming Du.Asymmetric Friedel–Crafts Alkylation of Indoles with Nitrodienes and 2‐Propargyloxy‐β‐nitrostyrenes Catalyzed by Diphenylamine‐Linked Bis(oxazoline)–Zn-(OTf)<sub>2</sub> Complexes[J].Eur J Org Chem.2012(21)
  • 4PabloEtayo,RamónBadorrey,María D.Díaz‐de‐Villegas,José A.Gálvez.Chiral Amino Diol Derivatives as New Modular Organocatalysts for the Enantioselective α‐Chlorination of Cyclic β‐Keto Esters[J].Adv Synth Catal.2010(18)
  • 5Ming-Hui Qi,Fei-Jun Wang,Min Shi.Synthesis of novel chiral oxazoline-Schiff base ligands for the catalytic asymmetric chlorination of β-keto esters[J].Tetrahedron: Asymmetry.2010(2)
  • 6HanLiu,Shao‐FengLu,JiaxiXu,Da‐MingDu.Asymmetric Friedel–Crafts Alkylation of Electron‐Rich N‐Heterocycles with Nitroalkenes Catalyzed by Diphenylamine‐Tethered Bis(oxazoline) and Bis(thiazoline) Zn<sup>II</sup> Complexes[J].Chem Asian J.2008(7)
  • 7Linge Ma,Peng Jiao,Qihan Zhang,Da-Ming Du,Jiaxi Xu.Ligand and substrate π-stacking interaction controlled enantioselectivity in the asymmetric aziridination[J].Tetrahedron: Asymmetry.2007(7)
  • 8Gabriela Guillena,Diego J. Ramón.Enantioselective α-heterofunctionalisation of carbonyl compounds: organocatalysis is the simplest approach[J].Tetrahedron: Asymmetry.2006(10)
  • 9Linge Ma,Peng Jiao,Qihan Zhang,Jiaxi Xu.Rigid backbone 1,8-anthracene-linked bis-oxazolines (AnBOXes): design, synthesis, application and characteristics in catalytic asymmetric aziridination[J].Tetrahedron: Asymmetry.2005(22)
  • 10StefanFrance,AnthonyWeatherwax,ThomasLectka.Recent Developments in Catalytic, Asymmetric α‐Halogenation: A New Frontier in Asymmetric Catalysis[J].Eur J Org Chem.2005(3)

二级参考文献8

  • 1[1](a) A.K.Ghosh, P.Mathivanan, J.Cappiello, Tetrahedron: Asymmetry, 1998, 9, 1.(b) J.S.Johnson, D.A.Evas, Acc.Chem.Res., 2000, 33, 325.(c) F.Fache, E.Schulz, L.Tommasino, M.Lemaire, Chem.Rev., 2000, 100, 2159.
  • 2[2](a) M.Reuman, A.I.Meyers, Tetrahedron, 1985, 41, 837.(b) P.Breton, C.Andre-Barres, Y.Langlois, Synth.Commun., 1992, 22, 2543.(c) R.C.F.Jones, G.J.Ward, Tetrahedron Lett., 1988, 29, 3853.d) T.G.Gant, A.I.Meyers, Tetrahedron, 1994, 50, 2297.
  • 3[3]S.E.Denmark, N.Nakajimn, O.J.Nicoise, A.M.Paucher, J.P.Edwards, J.Org.Chem., 1995, 60, 4884.
  • 4[4]Y.Imai, W.B.Zhang, T.Kida, Y.Nakatsuji, I.Ikeda, Tetrahedron: Asymmetry, 1996, 7(8), 2453.
  • 5[5](a) D.M.Du, B.Fu, W.T.Hua, Tetrahedron, 2003, 59(11), 1933.(b) B.Fu, D.M.Du, Chinese J.Chem., 2003, 21(6), 597.
  • 6[6]Spectral data (200 MHz for 1H NMR and 50 MHz for 13C NMR in CDCl3, δ ppm): 4: 1H NMR 8.59 (s, 2H, CONH), 7.50-7.25 (m, 8H, ArH), 6.63 (d, 2H, J =5.6 Hz, =CH2), 5.91 (d, 2H, J =2.0 Hz, =CH2), 3.87 (s, 6H, CO2Me), 3.48 (s, 2H, ArCH2), 2.85 (s, 2H, ArCH2).13C NMR: 172.99, 164.44, 140.41, 136.24, 130.76, 129.19, 128.17, 127.56, 127.24, 106.74, 52.77, 52.53, 34.05.MS (EI): m/z 448 (M+, 30), 320 (18), 219 (100), 191 (60).HRMS (EI): calcd.for C25H24N2O6 448.1634; found: 448.1631.3: 1H NMR: 7.40-7.26 (m, 8H, ArH), 6.97 (s, 2H, NH), 4.63 (t, 2H, J = 3.4 Hz, CHCO2Me), 4.06-3.95 (m, 4H, CH2OH), 3.79 (s, 6H, CO2Me), 3.52-2.80 (m, 6H, ArCH2 + OH).13C NMR: 171.36, 170.63, 140.30, 135.17, 130.18, 127.93, 127.51, 65.50, 61.93, 55.16, 52.69, 36.71.MS(FAB): m/z 485(M+1).Anal.calcd.for C25H28N2O8: C, 61.98; H, 5.78; N, 5.78.Found: C, 62.11; H, 5.92; N, 5.70.1a: 1H NMR: 7.41-7.12 (m, 8H, ArH), 4.76 (dd, 2H, J = 7.2, 7.4 Hz), 4.68-4.40 (m, 4H), 3.73 (s, 6H, CO2Me), 3.40-2.90 (m, 4H, ArCH2).13C NMR: 171.04, 169.15, 140.79, 135.12, 130.02, 127.94, 127.51, 127.15, 70.00, 68.02, 53.35, 52.51, 52.45, 37.58, 37.44.MS(EI): m/z 448 (M+, 35), 389 (M-59, 21), 320(M-128, 100); HRMS (EI) calcd.for C25H24N2O6 448.1634.Found: 448.1633.8: 1H NMR: 7.98 (m, 2H, ArH), 7.49-7.36 (m, 2H, ArH), 4.96 (dd, 2H, J = 6.2, 12.0 Hz), 4.73-4.52 (m, 4H), 3.82 (s, 3H, CO2CH3); 13C NMR: 171.2, 169.6, 140.7, 139.0, 130.9, 127.7, 127.2, 126.9, 52.7.HRMS (EI): calcd.for C11H11NO3 205.0739.Found: 205.0735.
  • 7[7]A.J.Philips, Y.Uto, P.Wipt, M.J.Reno, D.R.Williams, Org.Lett., 2000, 2(8), 1165.
  • 8[8]A.M.Harm, J.G.Knight, G.Stemp, Synlett, 1996, 677.Y.Imai, S.Matsuo, W.B.Zhang, Y.Nakatsuji, I.Ikeda, Synlett, 2000, 239.
Chinese Chemical Letters
2014年 第11期

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