Totally Selective Ring-Opening of Amino Epoxides with Ketones:  A General Entry to Enantiopure (2R,3S)- and (2S,3S)-3-Aminoalkano-1,2-diols

  1. José M. Concellón 1
  2. José Ramón Suárez 1
  3. Santiago García-Granda 1
  4. M. Rosario Díaz 1
  1. 1 Departamento de Química Orgánica e Inorgánica and Departamento de Química Física y Analítica, Facultad de Química, Universidad de Oviedo, Julián Clavería, 8, 33071 Oviedo, Spain
Revista:
Organic Letters

ISSN: 1523-7060,  1523-7052

Año de publicación: 2004

Volumen: 7

Número: 2

Páginas: 247-250

Tipo: Artículo

DOI: 10.1021/OL047785O GOOGLE SCHOLAR lock_openAcceso abierto editor

Otras publicaciones en: Organic Letters

Resumen

Transformation of enantiopure diastereoisomers (2R,1‘S)- and (2S,1‘S)-2-(1-aminoalkyl)epoxides into the corresponding 4-(1-aminoalkyl)-1,3-dioxolanes is achieved by reaction with different ketones in the presence of BF3·Et2O. The conversion takes place in very high yields, total selectivity, and without epimerization. A mechanism to explain this transformation is proposed. The obtained 1,3-dioxolanes can be deprotected, and (2R,3S)- and (2S,3S)-3-aminoalkano-1,2-diols were isolated.

Referencias bibliográficas

  • Torok D., (1993), J. Org. Chem., 58, pp. 7276, 10.1021/jo00077a060
  • Bogert M., (1933), J. Am. Chem. Soc., 55, pp. 3745, 10.1021/ja01336a047
  • Vyan J. R., (2003), J. Org. Chem., 68, pp. 9147
  • Nagata T., (1994), Bull. Chem. Soc. Jpn., 67, pp. 2616
  • Iranpoor N., (1998), J. Chem. Res., Synop., 466, pp. 467
  • Habibi M., (1975), Catal. Lett., 3, pp. 207
  • Adams R., (1999), J. Organomet. Chem., 582, pp. 361
  • Iranpoor N., (1998), Synth. Commun., 28, pp. 3193
  • Busci I., (2001), J. Mol. Catal., 168, pp. 52
  • Mohammadpoor-Baltork I., (2001), Synth. Commun., 31, pp. 3416, 10.1081/SCC-100106198
  • Firouzabadi H., (2002), Bull. Chem. Soc. Jpn., 75, pp. 2205
  • Tangestaninejad S., (2001), J. Chem. Res., Synop., 365, pp. 367
  • Zhu Z., (1997), Organometallics, 16, pp. 3663
  • Colvin E. W., (1983), J. Chem. Soc., Chem. Commun., 312, pp. 314
  • Barluenga J., (1994), J. Chem. Soc., Chem. Commun., 969, pp. 970
  • Barluenga J., (1995), J. Org. Chem., 60, pp. 6699, 10.1021/jo00126a019
  • Representative Experimental Procedure.To a stirred solution of the corresponding amino epoxide1or3(0.2 mmol) in CH2Cl2(1 mL, or propanone when this ketone was used), BF3·OEt2(0.025 mL, 0.2 mmol) and the corresponding ketone (0.22 mmol) were added at 0 °C. After 1 h of stirring, an aqueous saturated solution of sodium bicarbonate (5 mL) was added, and the mixture was stirred at room temperature for 5 min. Then, the aqueous phase was extracted with CH2Cl2(3 × 5 mL), and the combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Flash column chromatography on silica gel (hexane/EtOAc 20:1) provided pure compounds2and4.
  • These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or the Cambridge Data Centre, 12 Union Road