909038-82-0Relevant articles and documents
A practical synthesis of optically active arylglycines via catalytic asymmetric Strecker reaction
Banphavichit, Vorawit,Mansawat, Woraluk,Bhanthumnavin, Worawan,Vilaivan, Tirayut
experimental part, p. 5849 - 5854 (2009/12/01)
A practical procedure for catalytic asymmetric synthesis of optically active arylglycine derivatives via optically active α-aminonitriles has been developed. The N-benzhydryl α-arylaminonitrile intermediates were prepared in excellent yield (89-99%) and enantiomeric purity (96 to >98% ee) by enantioselective cyanation of aldimines with TMSCN/iPrOH in the presence of 2.5 mol % of an easily prepared Ti/chiral amino alcohol complex at 0 °C, without requiring slow addition of the cyanating agent. The easily racemized α-aminonitrile intermediates were efficiently hydrolyzed by an aqueous HCl/TFA mixture to give the arylglycine derivatives in good yield (60-92%) and moderate to excellent enantiomeric purity (85-98% ee).
Synthesis of α-amino acid precursors directly from aldehydes using masked acyl cyanide reagents and N,O-dialkylated hydroxylamines
Nemoto, Hisao,Ma, Rujian,Kawamura, Tomoyuki,Kamiya, Masaki,Shibuya, Masayuki
, p. 6038 - 6043 (2007/10/03)
A 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 co
