499783-31-2Relevant 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 (2007/10/03)
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 anti-β-amino-α-hydroxy acid derivatives using nucleophilic epoxidation of 1-arylthio-1-nitroalkenes
Ambroise, Lydia,Jackson, Richard F.W.
, p. 2311 - 2314 (2007/10/03)
Reaction of lithium t-butylperoxide with 1-arylthio-1-nitroalkenes 5, prepared by condensation of (4-tolylthio)nitromethane with N-(Boc)-protected α-amino aldehydes, leads to the formation of oxazolidinones rather than the expected oxitranes. Initially, a mixture of cis 8 and trans 9 diastereoisomers is formed, but upon exposure to silica gel complete conversion to the cis-diastereoisomers 8 takes place.
