434930-39-9Relevant academic research and scientific papers
Synthesis of optically active C-allylglycine derivatives and conversion into isoquinolones
Zhang, Nong,Nubbemeyer, Udo
, p. 242 - 252 (2002)
C-Allylglycyl amides can be efficiently synthesized via an auxiliary controlled diastereoselective aza-Claisen rearrangement. The stereodirecting unit is placed on an auxiliary derived from commercially available (S)-proline. After N-allylation, the obtained optically active allylamines were reacted with various N-protected glycyl fluorides to give the (2R)-C-allylglycyl amides in good yields. The diastereoselectivity of the asymmetric allylation varied between 1:1 and > 1:15 depending on the N-protective group, the auxiliary, and the reaction temperature. Likewise, the C-allylglycine derivatives can be used as monomers in peptide synthesis to synthesize (R)-proline derivatives or chiral isoquinolones; the latter should serve as building blocks in the total syntheses of alkaloids.
