917027-01-1Relevant articles and documents
A practical synthesis of optically active arylglycines via catalytic asymmetric Strecker reaction
Banphavichit, Vorawit,Mansawat, Woraluk,Bhanthumnavin, Worawan,Vilaivan, Tirayut
, p. 5849 - 5854 (2009)
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).
