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Synthesis 2001(6): 0831-0832
DOI: 10.1055/s-2001-13414
DOI: 10.1055/s-2001-13414
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
Cerium Chloride-Catalysed Cleavage of Epoxides with Aromatic Amines
Further Information
Received
26 January 2001
Publication Date:
15 October 2004 (online)
Publication History
Publication Date:
15 October 2004 (online)
Abstract
Cerium chloride has been demonstrated for the first time as an efficient catalyst for the ring opening of epoxides with aromatic amines to generate β-amino alcohols.
Key words
epoxide - aromatic amine - cerium chloride - β-amino alcohol
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References
Representative data for compound 3d: Pale yellow viscous liquid. IR(neat): ν = 3140-3610 cm- 1. 1H NMR (200 MHz, CDCl3): δ = 1.08 (m, 1H), 1.38 (m, 3H), 1.79 (m, 2H), 2.12 (m, 2H), 2.91 (br s, 2H, NH and OH), 3.11 (ddd, 1H, J = 10.9, 9.3, 3.9 Hz, CH-NHPh), 3.41 (ddd, 1H, J = 9.6,9.6, 3.9 Hz, CH-OH), 3.85 (s, 3H), 6.76 (m, 4H). MS (EI): m/z = 221(M+). HRMS: m/z calcd for C13H19NO2 (M+) 221.141579; found: 221.141048.