Metalloporphyrin as an efficient catalyst in the regioselective isomerization of epoxides to carbonyl compounds

Chemistry Letters

Volumn , Issue 12, 1996, Pages 1031-1032

  Takanami, Toshikatsu ^a   Hirabe, Rina ^a   Ueno, Masayoshi ^a   Hino, Fumio ^a   Suda, Kohji ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000695467     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.1031     Document Type: Article

References (13)

1. a) B. Rickborn, in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, New York (1991), Vol. 3, p. 733.
2. b) J. G. Smith, Synthesis, 1984, 629, and references cited therein.
3. Following Lewis and none-Lewis acid catalyzed reactions have been reported, a) [Pd(0) complexes] S. Kulasegaram, and R. Kulawiec, J. Org. Chem., 59, 7195 (1994).
4. b) [Tris-(pentafluorophenyl)boron] K. Ishihara, N. Hanaki, and H. Yamamoto, Synlett, 1995, 721.
5. c) [EGA (electrogenerated acid)] K. Uneyama, A. Ishimura, K. Fujii, and S. Torii, Tetrahedron Lett., 24, 2857 (1983).
6. 4] T. Inokuchi, M. Kusumoto, S. Matsumoto, H. Okada, and S. Torii, Chem. Lett., 1991, 2009.
7. e) [TCNE (tetracyanoethylene)] Y. Masaki, T. Miura, and M. Ochiai, Chem. Lett., 1993, 17, and references cited therein.
8. Several Lewis-acid reagents have been reported for the regioselective isomerization of epoxides. a) [Organoboron reagents] see Ref. 2b.
9. b) [Organoaluminum reagents] K. Maruoka, N. Murase, R. Bureau, T. Ooi, and H. Yamamoto, Tetrahedron, 50, 3663 (1994).
10. 4 in ether] R. Sudha, K. M. Narasimhan, V. G. Saraswathy, and S. Sankararaman, J. Org. Chem., 61, 1877 (1996), and references cited therein.
11. K. Suda, M. Sashima, M. Izutsu, and F. Hino, J. Chem. Soc., Chem. Commun., 1994, 949.
12. 2). These complexes were characterized by UV-VIS spectroscopy, cyclic voltammetry and elemental analysis.
13. 3) data of 2a and 2b are as follows. 2a: δ 0.12 (6H, s), 0.97 (9H, s), 3.86 (2H, s), 4.29 (2H, s), 7.25-7.41 (5H, m); 2b: δ 1.33 (3H, d, J = 6.6 Hz), 3.75 and 3.90 (each 1H, d, J = 16.5 Hz), 4.47 (1H, q, J = 6.6 Hz), 6.97-7.67 (20H, m).