Regioselective Epoxide Ring Opening. Steroselective Synthesis of a Tetrahydropyran Ring

Journal of Heterocyclic Chemistry

Volumn 35, Issue 4, 1998, Pages 865-869

  Gruttadauria, Michelangelo ^a   Noto, Renato ^a   Riela, Serena ^a  

^a UNIVERSITY OF PALERMO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0004602054     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570350414     Document Type: Article

References (7)

1. J.-C. Harmange, B. Figadére, Tetrahedron Asymmetry, 4, 1711 (1993).
2. T. L. B. Boivin, Tetrahedron, 43, 3309, (1987).
3. L. Arista, M. Gruttadauria and E. J. Thomas, Synlett, 627 (1997).
4. K. Bratt, A. Garavelas, P. Perlmutter and G. Westman, J. Org. Chem., 61, 2109 (1996).
5. A. S. Rao in Comprehensive Organic Synthesis, Vol 7, Chapter 3.1, B. M. Trost and I. Fleming, eds, Pergamon Press, New York, 1991, p. 368.
6. 1H-nmr: δ 1.23 (d, 3H, J = 6.3 Hz), 1.43-1.82 (m, 7H), 2.94 (s, 3H), 3.64 (t, 2H, J = 6.0 Hz), 3.73 (quint, 1H, J = 6.3 Hz), 4.47 and 4.66 (d, each 1H, J = 11.5 Hz), 4.58-4.65 (m, 1H), 7.26-7.36 (m, 5H).
7. J. Eames, R. V. H. Jones and S. Warren, Tetrahedron Letters, 37, 4823 (1996) and references therein.