The preparation of β-hydroxysulfoxides

Synthetic Communications

Volumn 27, Issue 16, 1997, Pages 2857-2863

  Gabbi, Cristina ^a   Ghelfi, Franco ^a   Grandi, Romano ^a  

^a UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

SULFIDE;

ARTICLE; DRUG SYNTHESIS; NONHUMAN; OXIDATION; REACTION ANALYSIS; RESIDUE ANALYSIS; SULFATION;

EID: 0030740217     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708004162     Document Type: Article

References (36)

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6. Mitra R.B., Muljiani Z., Deshmukh A.R.A.S., Joshi V.S., Gadre S.R., Synth. Commun. 1984, 14(2), 101; Alvarez-Ibarra C., Cuervo-Rodriguez R., Fernandez-Monreal M.C., and Ruiz M.P., J. Org. Chem. 1994, 59, 7284; Conte V.. Di Furia F., Licini G., Modena G., Sbampato G., and Valle G., Tetrahedron Asimmetry 1991, Vol.2, No.4, 257; Iriuchijima S., Maniwa K., and Tsuchihashi G., J. Amer. Chem. Soc. 1974, 96, 4820; Garcia Ruano J.L., Phosphorous, Sulfur, Silicon, Relat. Elements 1993, 74, 233; Solladie G., Almario A., and Dominguez C., Pure Appl. Chem., 1994, 66, 2159; Demailly G., Greck C., and Solladie G., Tetrahedron Letters 1984, Vol.25, No 37, 4113 ; Solladie G., Greek C., Demailly G., and Solladiè-Cavallo A., Tetrahedron Letters 1982, Vol.23, No 48, 5047; Solladie G., Demailly G., and Greek C., Tetrahedron Letters 1985, Vol.26, No 4, 435; Kingsbury C.A., J. Org. Chem. 1993, 58, 5628;
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9. Mitra R.B., Muljiani Z., Deshmukh A.R.A.S., Joshi V.S., Gadre S.R., Synth. Commun. 1984, 14(2), 101; Alvarez-Ibarra C., Cuervo-Rodriguez R., Fernandez-Monreal M.C., and Ruiz M.P., J. Org. Chem. 1994, 59, 7284; Conte V.. Di Furia F., Licini G., Modena G., Sbampato G., and Valle G., Tetrahedron Asimmetry 1991, Vol.2, No.4, 257; Iriuchijima S., Maniwa K., and Tsuchihashi G., J. Amer. Chem. Soc. 1974, 96, 4820; Garcia Ruano J.L., Phosphorous, Sulfur, Silicon, Relat. Elements 1993, 74, 233; Solladie G., Almario A., and Dominguez C., Pure Appl. Chem., 1994, 66, 2159; Demailly G., Greck C., and Solladie G., Tetrahedron Letters 1984, Vol.25, No 37, 4113 ; Solladie G., Greek C., Demailly G., and Solladiè-Cavallo A., Tetrahedron Letters 1982, Vol.23, No 48, 5047; Solladie G., Demailly G., and Greek C., Tetrahedron Letters 1985, Vol.26, No 4, 435; Kingsbury C.A., J. Org. Chem. 1993, 58, 5628;
10. Mitra R.B., Muljiani Z., Deshmukh A.R.A.S., Joshi V.S., Gadre S.R., Synth. Commun. 1984, 14(2), 101; Alvarez-Ibarra C., Cuervo-Rodriguez R., Fernandez-Monreal M.C., and Ruiz M.P., J. Org. Chem. 1994, 59, 7284; Conte V.. Di Furia F., Licini G., Modena G., Sbampato G., and Valle G., Tetrahedron Asimmetry 1991, Vol.2, No.4, 257; Iriuchijima S., Maniwa K., and Tsuchihashi G., J. Amer. Chem. Soc. 1974, 96, 4820; Garcia Ruano J.L., Phosphorous, Sulfur, Silicon, Relat. Elements 1993, 74, 233; Solladie G., Almario A., and Dominguez C., Pure Appl. Chem., 1994, 66, 2159; Demailly G., Greck C., and Solladie G., Tetrahedron Letters 1984, Vol.25, No 37, 4113 ; Solladie G., Greek C., Demailly G., and Solladiè-Cavallo A., Tetrahedron Letters 1982, Vol.23, No 48, 5047; Solladie G., Demailly G., and Greek C., Tetrahedron Letters 1985, Vol.26, No 4, 435; Kingsbury C.A., J. Org. Chem. 1993, 58, 5628;
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14. Iriuchijima S., Maniwa K., and Tsuchihashi G., J. Amer. Chem. Soc. 1974, 96, 4820; Russel G.A., and Ochrymowycz L.A., J. Org. Chem. 1970, 35, 764; Russel G.A., and Ochrymowycz L.A., J. Org.Chem. 1969, 34, 3618; Coldham I., and Warren S., J.Chem. Soc. Perkin Trans 1 1993, 1637; Tsuchihashi G., mitamura S., and Ogura K., Tetrahedron Letters 1973, No.4, 323; Alvarez-Ibarra C., Cuervo-Rodriguez R., Fernandez-Monreal M.C., and Ruiz M.P., J. Org.Chem. 1994, 59, 7284; Demailly G., Greek C., and Solladie G., Tetrahedron Letters 1984, Vol.25. No 37, 4113; Solladiè G., Greek C.. Demailly G., and Solladiè-Cavallo A., Tetrahedron Letters, 1982, Vol.23, No 48, 5047; Solladiè G., Demailly G., and Greek C., Tetrahedron Letters, 1985, Vol.26, 435; Kingsbury C. A., J. Org. Chem., 1972, Vol.37, No. 1, 102; Annunziata R., Cinquini M., and Cozzi F., J.C.S. Perkin I 1979, 1687; Tanikaga R., Sughara H., Tanaka K., and Kaji A., Synthesis 1977, 299.
15. Iriuchijima S., Maniwa K., and Tsuchihashi G., J. Amer. Chem. Soc. 1974, 96, 4820; Russel G.A., and Ochrymowycz L.A., J. Org. Chem. 1970, 35, 764; Russel G.A., and Ochrymowycz L.A., J. Org.Chem. 1969, 34, 3618; Coldham I., and Warren S., J.Chem. Soc. Perkin Trans 1 1993, 1637; Tsuchihashi G., mitamura S., and Ogura K., Tetrahedron Letters 1973, No.4, 323; Alvarez-Ibarra C., Cuervo-Rodriguez R., Fernandez-Monreal M.C., and Ruiz M.P., J. Org.Chem. 1994, 59, 7284; Demailly G., Greek C., and Solladie G., Tetrahedron Letters 1984, Vol.25. No 37, 4113; Solladiè G., Greek C.. Demailly G., and Solladiè-Cavallo A., Tetrahedron Letters, 1982, Vol.23, No 48, 5047; Solladiè G., Demailly G., and Greek C., Tetrahedron Letters, 1985, Vol.26, 435; Kingsbury C. A., J. Org. Chem., 1972, Vol.37, No. 1, 102; Annunziata R., Cinquini M., and Cozzi F., J.C.S. Perkin I 1979, 1687; Tanikaga R., Sughara H., Tanaka K., and Kaji A., Synthesis 1977, 299.
16. Iriuchijima S., Maniwa K., and Tsuchihashi G., J. Amer. Chem. Soc. 1974, 96, 4820; Russel G.A., and Ochrymowycz L.A., J. Org. Chem. 1970, 35, 764; Russel G.A., and Ochrymowycz L.A., J. Org.Chem. 1969, 34, 3618; Coldham I., and Warren S., J.Chem. Soc. Perkin Trans 1 1993, 1637; Tsuchihashi G., mitamura S., and Ogura K., Tetrahedron Letters 1973, No.4, 323; Alvarez-Ibarra C., Cuervo-Rodriguez R., Fernandez-Monreal M.C., and Ruiz M.P., J. Org.Chem. 1994, 59, 7284; Demailly G., Greek C., and Solladie G., Tetrahedron Letters 1984, Vol.25. No 37, 4113; Solladiè G., Greek C.. Demailly G., and Solladiè-Cavallo A., Tetrahedron Letters, 1982, Vol.23, No 48, 5047; Solladiè G., Demailly G., and Greek C., Tetrahedron Letters, 1985, Vol.26, 435; Kingsbury C. A., J. Org. Chem., 1972, Vol.37, No. 1, 102; Annunziata R., Cinquini M., and Cozzi F., J.C.S. Perkin I 1979, 1687; Tanikaga R., Sughara H., Tanaka K., and Kaji A., Synthesis 1977, 299.
17. Iriuchijima S., Maniwa K., and Tsuchihashi G., J. Amer. Chem. Soc. 1974, 96, 4820; Russel G.A., and Ochrymowycz L.A., J. Org. Chem. 1970, 35, 764; Russel G.A., and Ochrymowycz L.A., J. Org.Chem. 1969, 34, 3618; Coldham I., and Warren S., J.Chem. Soc. Perkin Trans 1 1993, 1637; Tsuchihashi G., mitamura S., and Ogura K., Tetrahedron Letters 1973, No.4, 323; Alvarez-Ibarra C., Cuervo-Rodriguez R., Fernandez-Monreal M.C., and Ruiz M.P., J. Org.Chem. 1994, 59, 7284; Demailly G., Greek C., and Solladie G., Tetrahedron Letters 1984, Vol.25. No 37, 4113; Solladiè G., Greek C.. Demailly G., and Solladiè-Cavallo A., Tetrahedron Letters, 1982, Vol.23, No 48, 5047; Solladiè G., Demailly G., and Greek C., Tetrahedron Letters, 1985, Vol.26, 435; Kingsbury C. A., J. Org. Chem., 1972, Vol.37, No. 1, 102; Annunziata R., Cinquini M., and Cozzi F., J.C.S. Perkin I 1979, 1687; Tanikaga R., Sughara H., Tanaka K., and Kaji A., Synthesis 1977, 299.
18. Iriuchijima S., Maniwa K., and Tsuchihashi G., J. Amer. Chem. Soc. 1974, 96, 4820; Russel G.A., and Ochrymowycz L.A., J. Org. Chem. 1970, 35, 764; Russel G.A., and Ochrymowycz L.A., J. Org.Chem. 1969, 34, 3618; Coldham I., and Warren S., J.Chem. Soc. Perkin Trans 1 1993, 1637; Tsuchihashi G., mitamura S., and Ogura K., Tetrahedron Letters 1973, No.4, 323; Alvarez-Ibarra C., Cuervo-Rodriguez R., Fernandez-Monreal M.C., and Ruiz M.P., J. Org.Chem. 1994, 59, 7284; Demailly G., Greek C., and Solladie G., Tetrahedron Letters 1984, Vol.25. No 37, 4113; Solladiè G., Greek C.. Demailly G., and Solladiè-Cavallo A., Tetrahedron Letters, 1982, Vol.23, No 48, 5047; Solladiè G., Demailly G., and Greek C., Tetrahedron Letters, 1985, Vol.26, 435; Kingsbury C. A., J. Org. Chem., 1972, Vol.37, No. 1, 102; Annunziata R., Cinquini M., and Cozzi F., J.C.S. Perkin I 1979, 1687; Tanikaga R., Sughara H., Tanaka K., and Kaji A., Synthesis 1977, 299.
19. Iriuchijima S., Maniwa K., and Tsuchihashi G., J. Amer. Chem. Soc. 1974, 96, 4820; Russel G.A., and Ochrymowycz L.A., J. Org. Chem. 1970, 35, 764; Russel G.A., and Ochrymowycz L.A., J. Org.Chem. 1969, 34, 3618; Coldham I., and Warren S., J.Chem. Soc. Perkin Trans 1 1993, 1637; Tsuchihashi G., mitamura S., and Ogura K., Tetrahedron Letters 1973, No.4, 323; Alvarez-Ibarra C., Cuervo-Rodriguez R., Fernandez-Monreal M.C., and Ruiz M.P., J. Org.Chem. 1994, 59, 7284; Demailly G., Greek C., and Solladie G., Tetrahedron Letters 1984, Vol.25. No 37, 4113; Solladiè G., Greek C.. Demailly G., and Solladiè-Cavallo A., Tetrahedron Letters, 1982, Vol.23, No 48, 5047; Solladiè G., Demailly G., and Greek C., Tetrahedron Letters, 1985, Vol.26, 435; Kingsbury C. A., J. Org. Chem., 1972, Vol.37, No. 1, 102; Annunziata R., Cinquini M., and Cozzi F., J.C.S. Perkin I 1979, 1687; Tanikaga R., Sughara H., Tanaka K., and Kaji A., Synthesis 1977, 299.
20. Iriuchijima S., Maniwa K., and Tsuchihashi G., J. Amer. Chem. Soc. 1974, 96, 4820; Russel G.A., and Ochrymowycz L.A., J. Org. Chem. 1970, 35, 764; Russel G.A., and Ochrymowycz L.A., J. Org.Chem. 1969, 34, 3618; Coldham I., and Warren S., J.Chem. Soc. Perkin Trans 1 1993, 1637; Tsuchihashi G., mitamura S., and Ogura K., Tetrahedron Letters 1973, No.4, 323; Alvarez-Ibarra C., Cuervo-Rodriguez R., Fernandez-Monreal M.C., and Ruiz M.P., J. Org.Chem. 1994, 59, 7284; Demailly G., Greek C., and Solladie G., Tetrahedron Letters 1984, Vol.25. No 37, 4113; Solladiè G., Greek C.. Demailly G., and Solladiè-Cavallo A., Tetrahedron Letters, 1982, Vol.23, No 48, 5047; Solladiè G., Demailly G., and Greek C., Tetrahedron Letters, 1985, Vol.26, 435; Kingsbury C. A., J. Org. Chem., 1972, Vol.37, No. 1, 102; Annunziata R., Cinquini M., and Cozzi F., J.C.S. Perkin I 1979, 1687; Tanikaga R., Sughara H., Tanaka K., and Kaji A., Synthesis 1977, 299.
21. Iriuchijima S., Maniwa K., and Tsuchihashi G., J. Amer. Chem. Soc. 1974, 96, 4820; Russel G.A., and Ochrymowycz L.A., J. Org. Chem. 1970, 35, 764; Russel G.A., and Ochrymowycz L.A., J. Org.Chem. 1969, 34, 3618; Coldham I., and Warren S., J.Chem. Soc. Perkin Trans 1 1993, 1637; Tsuchihashi G., mitamura S., and Ogura K., Tetrahedron Letters 1973, No.4, 323; Alvarez-Ibarra C., Cuervo-Rodriguez R., Fernandez-Monreal M.C., and Ruiz M.P., J. Org.Chem. 1994, 59, 7284; Demailly G., Greek C., and Solladie G., Tetrahedron Letters 1984, Vol.25. No 37, 4113; Solladiè G., Greek C.. Demailly G., and Solladiè-Cavallo A., Tetrahedron Letters, 1982, Vol.23, No 48, 5047; Solladiè G., Demailly G., and Greek C., Tetrahedron Letters, 1985, Vol.26, 435; Kingsbury C. A., J. Org. Chem., 1972, Vol.37, No. 1, 102; Annunziata R., Cinquini M., and Cozzi F., J.C.S. Perkin I 1979, 1687; Tanikaga R., Sughara H., Tanaka K., and Kaji A., Synthesis 1977, 299.
22. Iriuchijima S., Maniwa K., and Tsuchihashi G., J. Amer. Chem. Soc. 1974, 96, 4820; Russel G.A., and Ochrymowycz L.A., J. Org. Chem. 1970, 35, 764; Russel G.A., and Ochrymowycz L.A., J. Org.Chem. 1969, 34, 3618; Coldham I., and Warren S., J.Chem. Soc. Perkin Trans 1 1993, 1637; Tsuchihashi G., mitamura S., and Ogura K., Tetrahedron Letters 1973, No.4, 323; Alvarez-Ibarra C., Cuervo-Rodriguez R., Fernandez-Monreal M.C., and Ruiz M.P., J. Org.Chem. 1994, 59, 7284; Demailly G., Greek C., and Solladie G., Tetrahedron Letters 1984, Vol.25. No 37, 4113; Solladiè G., Greek C.. Demailly G., and Solladiè-Cavallo A., Tetrahedron Letters, 1982, Vol.23, No 48, 5047; Solladiè G., Demailly G., and Greek C., Tetrahedron Letters, 1985, Vol.26, 435; Kingsbury C. A., J. Org. Chem., 1972, Vol.37, No. 1, 102; Annunziata R., Cinquini M., and Cozzi F., J.C.S. Perkin I 1979, 1687; Tanikaga R., Sughara H., Tanaka K., and Kaji A., Synthesis 1977, 299.
23. Iriuchijima S., Maniwa K., and Tsuchihashi G., J. Amer. Chem. Soc. 1974, 96, 4820; Russel G.A., and Ochrymowycz L.A., J. Org. Chem. 1970, 35, 764; Russel G.A., and Ochrymowycz L.A., J. Org.Chem. 1969, 34, 3618; Coldham I., and Warren S., J.Chem. Soc. Perkin Trans 1 1993, 1637; Tsuchihashi G., mitamura S., and Ogura K., Tetrahedron Letters 1973, No.4, 323; Alvarez-Ibarra C., Cuervo-Rodriguez R., Fernandez-Monreal M.C., and Ruiz M.P., J. Org.Chem. 1994, 59, 7284; Demailly G., Greek C., and Solladie G., Tetrahedron Letters 1984, Vol.25. No 37, 4113; Solladiè G., Greek C.. Demailly G., and Solladiè-Cavallo A., Tetrahedron Letters, 1982, Vol.23, No 48, 5047; Solladiè G., Demailly G., and Greek C., Tetrahedron Letters, 1985, Vol.26, 435; Kingsbury C. A., J. Org. Chem., 1972, Vol.37, No. 1, 102; Annunziata R., Cinquini M., and Cozzi F., J.C.S. Perkin I 1979, 1687; Tanikaga R., Sughara H., Tanaka K., and Kaji A., Synthesis 1977, 299.
24. Iriuchijima S., Maniwa K., and Tsuchihashi G., J. Amer. Chem. Soc. 1974, 96, 4820; Russel G.A., and Ochrymowycz L.A., J. Org. Chem. 1970, 35, 764; Russel G.A., and Ochrymowycz L.A., J. Org.Chem. 1969, 34, 3618; Coldham I., and Warren S., J.Chem. Soc. Perkin Trans 1 1993, 1637; Tsuchihashi G., mitamura S., and Ogura K., Tetrahedron Letters 1973, No.4, 323; Alvarez-Ibarra C., Cuervo-Rodriguez R., Fernandez-Monreal M.C., and Ruiz M.P., J. Org.Chem. 1994, 59, 7284; Demailly G., Greek C., and Solladie G., Tetrahedron Letters 1984, Vol.25. No 37, 4113; Solladiè G., Greek C.. Demailly G., and Solladiè-Cavallo A., Tetrahedron Letters, 1982, Vol.23, No 48, 5047; Solladiè G., Demailly G., and Greek C., Tetrahedron Letters, 1985, Vol.26, 435; Kingsbury C. A., J. Org. Chem., 1972, Vol.37, No. 1, 102; Annunziata R., Cinquini M., and Cozzi F., J.C.S. Perkin I 1979, 1687; Tanikaga R., Sughara H., Tanaka K., and Kaji A., Synthesis 1977, 299.
25. Iriuchijima S., Maniwa K., and Tsuchihashi G., J. Amer. Chem. Soc. 1974, 96, 4820; Russel G.A., and Ochrymowycz L.A., J. Org. Chem. 1970, 35, 764; Russel G.A., and Ochrymowycz L.A., J. Org.Chem. 1969, 34, 3618; Coldham I., and Warren S., J.Chem. Soc. Perkin Trans 1 1993, 1637; Tsuchihashi G., mitamura S., and Ogura K., Tetrahedron Letters 1973, No.4, 323; Alvarez-Ibarra C., Cuervo-Rodriguez R., Fernandez-Monreal M.C., and Ruiz M.P., J. Org.Chem. 1994, 59, 7284; Demailly G., Greek C., and Solladie G., Tetrahedron Letters 1984, Vol.25. No 37, 4113; Solladiè G., Greek C.. Demailly G., and Solladiè-Cavallo A., Tetrahedron Letters, 1982, Vol.23, No 48, 5047; Solladiè G., Demailly G., and Greek C., Tetrahedron Letters, 1985, Vol.26, 435; Kingsbury C. A., J. Org. Chem., 1972, Vol.37, No. 1, 102; Annunziata R., Cinquini M., and Cozzi F., J.C.S. Perkin I 1979, 1687; Tanikaga R., Sughara H., Tanaka K., and Kaji A., Synthesis 1977, 299.
26. Bellesia F., Ghelfi F., Pagnoni U.M., and Pinetti A., J. Chem. Res.(S), 1989, 108, 360; Bellesia F., Ghelfi F., Pagnoni U.M., and Pinetti A., Synth. Commun. 1991, 489; Bellesia F., Ghelfi F., Pagnoni U.M., and Pinetti A., J. Chem. Res.(S) 1990, 188; Bellesia F., Ghelfi F., Pagnoni U.M., and Pinetti A., Gazz. Chim. It., 1991, 121, 245; Bellesia F., Boni M., Ghelfi F., Grandi R., Pagnoni U.M., and Pinetti A., Tetrahedron 1992, 48, 4579.
27. Bellesia F., Ghelfi F., Pagnoni U.M., and Pinetti A., J. Chem. Res.(S), 1989, 108, 360; Bellesia F., Ghelfi F., Pagnoni U.M., and Pinetti A., Synth. Commun. 1991, 489; Bellesia F., Ghelfi F., Pagnoni U.M., and Pinetti A., J. Chem. Res.(S) 1990, 188; Bellesia F., Ghelfi F., Pagnoni U.M., and Pinetti A., Gazz. Chim. It., 1991, 121, 245; Bellesia F., Boni M., Ghelfi F., Grandi R., Pagnoni U.M., and Pinetti A., Tetrahedron 1992, 48, 4579.
28. Bellesia F., Ghelfi F., Pagnoni U.M., and Pinetti A., J. Chem. Res.(S), 1989, 108, 360; Bellesia F., Ghelfi F., Pagnoni U.M., and Pinetti A., Synth. Commun. 1991, 489; Bellesia F., Ghelfi F., Pagnoni U.M., and Pinetti A., J. Chem. Res.(S) 1990, 188; Bellesia F., Ghelfi F., Pagnoni U.M., and Pinetti A., Gazz. Chim. It., 1991, 121, 245; Bellesia F., Boni M., Ghelfi F., Grandi R., Pagnoni U.M., and Pinetti A., Tetrahedron 1992, 48, 4579.
29. Bellesia F., Ghelfi F., Pagnoni U.M., and Pinetti A., J. Chem. Res.(S), 1989, 108, 360; Bellesia F., Ghelfi F., Pagnoni U.M., and Pinetti A., Synth. Commun. 1991, 489; Bellesia F., Ghelfi F., Pagnoni U.M., and Pinetti A., J. Chem. Res.(S) 1990, 188; Bellesia F., Ghelfi F., Pagnoni U.M., and Pinetti A., Gazz. Chim. It., 1991, 121, 245; Bellesia F., Boni M., Ghelfi F., Grandi R., Pagnoni U.M., and Pinetti A., Tetrahedron 1992, 48, 4579.
30. Bellesia F., Ghelfi F., Pagnoni U.M., and Pinetti A., J. Chem. Res.(S), 1989, 108, 360; Bellesia F., Ghelfi F., Pagnoni U.M., and Pinetti A., Synth. Commun. 1991, 489; Bellesia F., Ghelfi F., Pagnoni U.M., and Pinetti A., J. Chem. Res.(S) 1990, 188; Bellesia F., Ghelfi F., Pagnoni U.M., and Pinetti A., Gazz. Chim. It., 1991, 121, 245; Bellesia F., Boni M., Ghelfi F., Grandi R., Pagnoni U.M., and Pinetti A., Tetrahedron 1992, 48, 4579.
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