Optically active nitroalkenes—synthesis, addition reactions and transformation into amino acids |
| |
Authors: | Jan Hü bner, Jü rgen Liebscher,Michael P tzel |
| |
Affiliation: | Institut für Chemie, Humboldt-Universität Berlin, Brook-Taylor-Strasse 2, D-12489, Berlin, Germany |
| |
Abstract: | Optically active nitroalkenes 4 were synthesized via Henry reaction. Conjugate addition of vinylmagnesium bromide to 4 gave nitroalkane syn-5 while cyclopropanation with sulfur ylides or dibromocarbene afforded nitrocyclopropanes 8, 10 and 11 in a diastereoselective manner. These products were used to synthesize optically active β-amino acids 7 and 16 as well as cyclopropane γ-amino acids 19 and 20 by reduction of the nitro group and oxidative cleavage of the dioxolane substituent. |
| |
Keywords: | cyclopropanation nitroolefines conjugate addition amino acids |
本文献已被 ScienceDirect 等数据库收录! |
|