jo0607515_si_001.pdf (2.27 MB)
Synthesis of α-Amino Acid Precursors Directly from Aldehydes Using Masked Acyl Cyanide Reagents and N,O-Dialkylated Hydroxylamines
journal contribution
posted on 2006-08-04, 00:00 authored by Hisao Nemoto, Rujian Ma, Tomoyuki Kawamura, Masaki Kamiya, Masayuki ShibuyaA synthetic methodology for the synthesis of α-amino acid precursors directly from the corresponding
aldehydes using N,O-dialkylated hydroxylamines and masked acyl cyanide (MAC) reagents was developed.
The one-pot reaction can be carried out under mild conditions and without a separate purification step of
the imino species. The method was applied to the synthesis of optically pure (+)-4-methylphenylglycine
and the derivatives by using an Abiko−Masamune's tricyclic 1,2-oxazolidine as the chiral auxiliary.