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Synlett 2004(5): 0846-0850  
DOI: 10.1055/s-2004-817780
LETTER
© Georg Thieme Verlag Stuttgart · New York

Transition Metal-based Lewis Acid Catalyzed Ring Opening of Epoxides Using Amines under Solvent-Free Conditions

Pei-Qing Zhao, Li-Wen Xu, Chun-Gu Xia*
State key laboratory of Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P. R. China
Fax: +86(931)8277088; e-Mail: cgxia@ns.lzb.ac.cn;
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Publication History

Received 18 December 2003
Publication Date:
17 February 2004 (online)

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Transition Metal-based Lewis Acid Catalyzed Ring Opening of Epoxides Using Amines Under Solvent-Free ConditionsSynlett 2004; 2004(06): 1122-1122
DOI: 10.1055/s-2004-822910

Abstract

Transition metal-based Lewis acids, such as SnCl4·5H2O, Co(OAc)2·4H2O, Ni(OAc)2·2H2O, NiCl2, Mn(OAc)2·4H2O etc. catalyze the nucleophilic opening of epoxide rings by amines leading to the efficient synthesis of β-amino alcohols. The reaction works well with aromatic and aliphatic amines in high yields under solvent-free conditions.

Key words

amino alcohols - amines - epoxides - Lewis acids - solvent-free

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Typical Experimental Procedure: A mixture of the phenyl glycidyl ether (2 mmol), the aniline (2.2 mmol), and SnCl4·5H2O (0.1 mmol, 5%mol) was stirred at 50 ° for 12 h. After completion of the reaction, as indicated by TLC, the reaction mixture was directly purified by column chromatography on silica gel (100-200mesh, EtOAc-petroleum ether) to afford corresponding β-amino alcohols. Selected spectra data: 1H NMR (400 MHz, CDCl3): δ = 3.24 (m, 1 H), 3.40 (m, 1 H), 3.61 (m, 2 H), 4.02 (m, 2 H), 4.22 (br s, 1 H), 6.65 (m, 2 H), 6.72 (m, 2 H), 6.90 (m, 2 H), 7.15 (m, 2 H), 7.26 (m, 2 H). 13C NMR (100 MHz, CDCl3): δ = 158.4, 148.0, 121.2, 118.4, 117.9, 115.0, 114.5, 113.2, 69.9, 60.3, 46.5. GC-MS: m/z = 243, 106, 94, 77, 65, 51. All other known compounds were fully characterized by GC-MS (Agilent 6890N GC/5973N MS, HP-5MS) and usual spectral methods.