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Antonioletti, R.; Bonadies, F.; Lattanzi, A.; Monteagudo, E.S.; Scettri, A. "Sharpless epoxidation by in situ generation of furylhydroperoxides" (1992) Tetrahedron Letters. 33(37):5433-5436
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Abstract:

The compatibility of the generation of furylhydroperoxides by a radical chain process with the presence of oxygen acceptors and transition metal catalysts allows the achievement of a modified Sharpless procedure for the epoxidation of allylic alcohols and oxidation of sulphides to sulphoxides. © 1992.

Registro:

Documento: Artículo
Título:Sharpless epoxidation by in situ generation of furylhydroperoxides
Autor:Antonioletti, R.; Bonadies, F.; Lattanzi, A.; 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:furan derivative; peroxide; article; priority journal; reaction analysis; synthesis
Año:1992
Volumen:33
Número:37
Página de inicio:5433
Página de fin:5436
DOI: http://dx.doi.org/10.1016/S0040-4039(00)79114-3
Título revista:Tetrahedron Letters
Título revista abreviado:Tetrahedron Lett.
ISSN:00404039
CODEN:TELEA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v33_n37_p5433_Antonioletti

Referencias:

  • Mimoun, Oxygen Transfer from Inorganic and Organic Peroxides to Organic Substrates: A Common Mechanism? (1982) Angewandte Chemie International Edition in English, 21, p. 734
  • Adam, Braun, Griesbeck, Lucchini, Staab, Will, (1989) J. Am. Chem. Soc., 111, p. 203. , For one-pot oxygen transfer process based on the employment of singlet oxygen see, and references therein
  • Antonioletti, Bonadies, Scettri, (1988) Tetrahedron Lett., 29, p. 4987
  • Antonioletti, Bonadies, Floro, Scettri, (1990) Gazz. Chim. It., 120, p. 471
  • Antonioletti, Bonadies, Scettri, (1991) Gazz. Chim. It., 121, p. 233
  • Rossiter, Verhoeven, Sharpless, (1979) Tetrahedron Lett., 20, p. 4733
  • Mihelich, (1979) Tetrahedron Lett., 20, p. 4729
  • This inversion of diastereoselectivity was observed in a more evident way by direct epoxidation of trans-3-penten-2-ol with furylhydroperoxide2a (R1 = -Me, R2 = -OEt, R3 = -Me) in presence of Ti(-OiPr)4 in dichloromethane solution at −17 °C for 17h: in fact the resulting epoxyalcohol was isolated in 42% yield as 21/79 erythro/threo mixture

Citas:

---------- APA ----------
Antonioletti, R., Bonadies, F., Lattanzi, A., Monteagudo, E.S. & Scettri, A. (1992) . Sharpless epoxidation by in situ generation of furylhydroperoxides. Tetrahedron Letters, 33(37), 5433-5436.
http://dx.doi.org/10.1016/S0040-4039(00)79114-3
---------- CHICAGO ----------
Antonioletti, R., Bonadies, F., Lattanzi, A., Monteagudo, E.S., Scettri, A. "Sharpless epoxidation by in situ generation of furylhydroperoxides" . Tetrahedron Letters 33, no. 37 (1992) : 5433-5436.
http://dx.doi.org/10.1016/S0040-4039(00)79114-3
---------- MLA ----------
Antonioletti, R., Bonadies, F., Lattanzi, A., Monteagudo, E.S., Scettri, A. "Sharpless epoxidation by in situ generation of furylhydroperoxides" . Tetrahedron Letters, vol. 33, no. 37, 1992, pp. 5433-5436.
http://dx.doi.org/10.1016/S0040-4039(00)79114-3
---------- VANCOUVER ----------
Antonioletti, R., Bonadies, F., Lattanzi, A., Monteagudo, E.S., Scettri, A. Sharpless epoxidation by in situ generation of furylhydroperoxides. Tetrahedron Lett. 1992;33(37):5433-5436.
http://dx.doi.org/10.1016/S0040-4039(00)79114-3