Zinc-catalyzed aminolysis of epoxides

Tetrahedron Letters

Volumn 44, Issue 32, 2003, Pages 6025-6027

  Pachón, Laura Durán ^a   Gamez, Patrick ^a   Van Brussel, Jos J M ^a   Reedijk, Jan ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

Author keywords

Aminolysis; Epoxide; Ring opening; Zinc catalyst

Indexed keywords

AMINE; AMINOALCOHOL; EPOXIDE; ZINC;

ARTICLE; CATALYSIS; CHELATION; GAS CHROMATOGRAPHY; RING OPENING; STEREOCHEMISTRY; SYNTHESIS;

EID: 0038644205     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01480-1     Document Type: Article

References (12)

1. Plucinska K., Kasprzykowski F., Kozian E. Tetrahedron Lett. 38:1997;861-864.
2. Bolli M.H., Ley S.V. J. Chem. Soc., Perkin Trans. 1. 1998;2243-2246.
3. Ghosh A.K., Wang Y. J. Org. Chem. 64:1999;2789-2795.
4. Yamaguchi T., Harada N., Ozaki K., Hashiyama T. Tetrahedron Lett. 39:1998;5575-5578.
5. Chang B.L., Ganesan A. Bioorg. Med. Chem. Lett. 7:1997;1511-1514.
6. 2).
7. 4].
8. 2AlCl).
9. 2}.
10. 2].
11. 1H NMR.
12. 3a: δ 3.74 (dd, J=11.0, 7.8 Hz, 1H), 3.92 (dd, J=11.0, 4.4 Hz, 1H), 4.52 (dd, J=7.8, 4.4 Hz, 1H), 6.5-7.5 (m, 10H) ppm; 3b: δ 3.5-3.9 (m, 2H), 3.45 (dd, J=6.7, 4.1 Hz, 1H), 6.9-7.4 (m, 9H) ppm; 3c: δ 0.95 (t, J=7.0 Hz, 6H), 1.2-1.4 (m, 8H), 3.78 (dd, J=11.0, 7.7 Hz, 1H), 3.90 (dd, J=10.8, 4.7 Hz, 1H), 4.52 (dd, J=7.7, 4.7 Hz, 1H), 6.7-7.2 (m, 5H) ppm; 3d: δ 3.55 (dd, J=10.6, 8.6 Hz, 1H), 3.59 (d, J=12.9 Hz, 1H), 3.7 (dd, J=10.6, 4.3 Hz, 1H), 3.77 (d, J=12.9 Hz, 1H), 3.82 (d, J=4.3 Hz, 1H), 7.0-7.6 (m, 10H) ppm; 3e: δ 1.16 (t, J=9.0 Hz, 3H), 3.8-4.1(m, 3H), 4.2 (q, J=9.0 Hz, 2H), 4.65 (d, J=6.8 Hz, 1H), 6.9-7.5 (m, 10H) ppm; 3f: δ 0.91 (t, J=7.0 Hz, 6H), 1.10-1.4 (m, 7H), 2.2-2.4 (m, 4H), 3.45 (d, J=13.8 Hz, 1H), 4.09 (d, J=13.8 Hz, 1H), 4.18 (q, J=9.0 Hz, 2H), 4.65 (d, J=11 Hz, 1H), 7.28-7.40 (m, 5H) ppm; 3g: δ 1.15 (t, J=8.9 Hz, 3H), 3.35 (d, J=13.9 Hz, 1H), 3.9 (d, J=13.9 Hz, 1H), 4.11 (d, J=6.7 Hz, 1H), 4.22 (q, J=8.9 Hz, 2H), 4.85 (br s, 1H), 7.25-7.43 (m, 10H) ppm; trans-3h: δ 1.0 (m, 1H), 1.34 (m, 3H), 1.76 (m, 2H), 2.1 (m, 2H), 2.80 (ddd, J=10.6, 9.8, 3.8 Hz, 1H), 3.3 (ddd, J=9.9, 9.8, 4.6 Hz, 1H), 6.75 (m, 3H), 7.1 (m, 2H) ppm; trans-3i: δ 0.90 (t, J=7.2 Hz, 6H), 1.1-1.4 (m, 7H), 1.6-1.8 (m, 4H), 2.12 (m, 1H), 2.2-2.4 (m, 4H), 3.31 (m, 1H), 4.07 (s, 1H) ppm; trans-3j: δ 1.08 (m, 1H), 1.34 (m, 3H), 1.40 (s, 2H), 1.79 (m, 2H), 2.1 (m, 2H), 2.85 (ddd, J=10.4, 9.7, 3.8 Hz, 1H), 3.3 (ddd, J=9.9, 9.7, 4.5 Hz, 1H), 7.06 (m, 5H) ppm.