499783-34-5Relevant academic research and scientific papers
Stereocontrolled synthesis of anti-α-hydroxy-β-amino and anti-α,β-diamino acid derivatives by epoxidation of 1-arylthio-1-nitroalkenes
Ambroise, Lydia,Dumez, Estelle,Szeki, Andrea,Jackson, Richard F. W.
, p. 2296 - 2308 (2002)
Epoxidation of 1-tolylthio-1-nitroalkenes containing an allylic Boc-protected amino group yields cis-oxazolidinones 13, formed by intramolecular trapping of the presumed intermediate epoxides by the carbamate group. Epoxidation of the analogous Z- or Fmoc-protected derivatives yields the corresponding syn-epoxides which, although they cannot be isolated, can be trapped with aqueous ammonia, or more efficiently benzylamine, to give stereoisomerically pure anti-α,β-diamino acid derivatives.
Stereoselective synthesis of differentially protected anti-α,β-diamino acid derivatives using arylthionitrooxiranes
Dumez,Szeki,Jackson
, p. 1214 - 1216 (2007/10/03)
Epoxidation of 1-tolylthio-1-nitroalkenes containing an allylic Z- or Fmoc-protected amino group yields the corresponding syn-epoxides which, although they cannot be isolated, can be trapped with aqueous ammonia to give stereoisomerically pure anti-α,β-diamino acid derivatives.
