Artículo
Antonioletti, R.; Bonadies, F.; Monteagudo, E.S.; Scettri, A. "Lithium iodide-catalyzed conjugate addition of β-dicarbonyl compounds" (1991) Tetrahedron Letters. 32(39):5373-5374
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Abstract:
Lithium iodide proves to be a very efficient catalyst for Michael addition of β-dicarbonyl compounds. The successful application of this methodology to α,β-unsaturated aldehdes allows an improved approach to 5,6-disubstituted cyclohex-2-en-1-ones. © 1991.
Registro:
| Documento: | Artículo |
| Título: | Lithium iodide-catalyzed conjugate addition of β-dicarbonyl compounds |
| Autor: | Antonioletti, R.; Bonadies, F.; Monteagudo, E.S.; Scettri, A. |
| Filiación: | Centro CNr di Studio per la Chimica delle Sostanze Organiche Naturali, Dipartimento di Chimica, Università La Sapienza, P.le A. Moro 5, 00185 Roma, Italy Departamento de Quimica Organica, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, Buenos Aires, Argentina |
| Palabras clave: | carboxylic acid derivative; cyclohexane derivative; ketone; article; priority journal; reaction analysis; synthesis |
| Año: | 1991 |
| Volumen: | 32 |
| Número: | 39 |
| Página de inicio: | 5373 |
| Página de fin: | 5374 |
| DOI: | http://dx.doi.org/10.1016/S0040-4039(00)92389-X |
| Título revista: | Tetrahedron Letters |
| Título revista abreviado: | Tetrahedron Lett. |
| ISSN: | 00404039 |
| CODEN: | TELEA |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v32_n39_p5373_Antonioletti |
Referencias:
- Watanabe, Miyazu, Irie, Michael additions catalyzed by metal(II) complexes. (1982) Bulletin of the Chemical Society of Japan, 55, p. 3212
- Boyer, Corrin, Perz, Réyé, CsF-promoted Michael addition in heterogeneous catalysis (1981) Journal of the Chemical Society, Chemical Communications, p. 122
- Nelson, Howell, De Lullo, Landen, Henry, (1980) J. Org. Chem., 45, p. 1246
- Coda, Desimoni, Righetti, Tacconi, (1984) Gazz. Chim. Ital., 114, p. 417
- Bergmann, Ginsburg, Pappo, (1959) Org. React., 10, pp. 179-557
- Kryshtal, Kulganek, Kucherov, Yanovskaya, Phase-Transfer Catalysis of the Michael Addition to α,β-Unsaturated Aldehydes (1979) Synthesis, p. 107
- For ex. ethyl 2-acethyl-5-oxo-hexanoate (entry a); IR (1%, CCl4: 1745, 1720 cm1. 1H-NMR, CDCl3): δ 4.17 (q, 2H; J = 7 Hz), 3.46 (t, 1H; J = 7 Hz), 2.47 (t, 2H; J = 7 Hz), 2.21 (s, 3H), 2.2-2.0 (m, 2H), 2.08 (s, 3H), 1.23 (t, 3H; J = 7 Hz). Ms (m/z): 200 (M+); Hauser, Pogany, 2-Hydroxy-6-methylbenzoic Acid Derivatives (1980) Synthesis, p. 814
- Gerhard, Muntwyler, Keller-Schierlein, (1975) Helv. Chim. Acta, 58, p. 1323
- On the ground of 1H-NMR data products 6 are obtained as 9:1 mixture of trans-cis stereoisomers
Citas:
---------- APA ----------
Antonioletti, R., Bonadies, F., Monteagudo, E.S. & Scettri, A. (1991) . Lithium iodide-catalyzed conjugate addition of β-dicarbonyl compounds. Tetrahedron Letters, 32(39), 5373-5374.http://dx.doi.org/10.1016/S0040-4039(00)92389-X
---------- CHICAGO ----------
Antonioletti, R., Bonadies, F., Monteagudo, E.S., Scettri, A. "Lithium iodide-catalyzed conjugate addition of β-dicarbonyl compounds" . Tetrahedron Letters 32, no. 39 (1991) : 5373-5374.http://dx.doi.org/10.1016/S0040-4039(00)92389-X
---------- MLA ----------
Antonioletti, R., Bonadies, F., Monteagudo, E.S., Scettri, A. "Lithium iodide-catalyzed conjugate addition of β-dicarbonyl compounds" . Tetrahedron Letters, vol. 32, no. 39, 1991, pp. 5373-5374.http://dx.doi.org/10.1016/S0040-4039(00)92389-X
---------- VANCOUVER ----------
Antonioletti, R., Bonadies, F., Monteagudo, E.S., Scettri, A. Lithium iodide-catalyzed conjugate addition of β-dicarbonyl compounds. Tetrahedron Lett. 1991;32(39):5373-5374.http://dx.doi.org/10.1016/S0040-4039(00)92389-X
