1392441-63-2Relevant academic research and scientific papers
An approach to chiral amino acids via reductive amination of ketones: Hydride reduction of 1-(S)-phenethyl amine derived Schiff bases of C-protected α-keto acids
Chandrasekhar, Sosale,Mohana Rao
, p. 1005 - 1009 (2012/09/22)
Various 1-acyl-2,4,10-trioxaadamantanes were prepared from the corresponding 1-methoxycarbonyl derivatives, via conversion to the N-acylpiperidine derivatives followed by reaction with a Grignard reagent in refluxing THF. These α-keto orthoformates were converted to the corresponding imines with 1-(S)-phenethyl amine (TiCl4/Et 3N/toluene/reflux), with the Schiff bases being reduced further with NaBH4 (MeOH/0 °C) into the corresponding 1-(S)-phenethyl amines (diastereomeric excess 91:9 by NMR). Hydrogenolysis of the phenethyl group (Pd-C/MeOH) finally led to the 1-(aminoalkyl)trioxaadamantanes, which are chiral C-protected α-amino acids, in excellent overall yields. 2012 Elsevier Ltd.
