B. Jiang, Y. Si
May 1, 2004
Citations
0
Influential Citations
31
Citations
Journal
Advanced Synthesis & Catalysis
Abstract
A new, inexpensive chiral amino alcohol-based ligand, (1S,2S)-2-N,N-dimethylamino-1-(4-nitrophenyl)-3-(tert-butyloxy)propan-1- ol, was developed for the asymmetric alkynylation of chloral in high yield with up to 98% ee. The resulting chiral adduct (S)-1-trichloromethyl-3-phenyl-2-propyn-1-ol was hydrogenated over 10% Pd/C to give the useful intermediate chiral trichloromethyl carbinol in quantitative yield, which was efficiently transformed into the pharmaceutically important building blocks 2-hydroxy-4-phenylbutanoate and homophenylalanine in high yield with excellent enantiomeric excess.