Assignment of the Absolute Configuration to Winterstein's Acid, R-3-Dimethylamino-3-phenyl Propionic Acid, by the Asymmetric Synthesis of Homochiral (S)-(+)-Ethyl 3-Dimethylamino-3-phenyl Propionate

Article abstract of DOI:10.1016/S0957-4166(00)86312-0

The asymmetric synthesis of homochiral (S)-(+)-ethyl 3-dimethylamino-3-phenyl propionate, via stereoselective Michael addition of lithium dimethylamide to (S)-Z-<(η⁵-C5H5)-Fe(CO)(PPh3)COCH=CHPh> and oxidative decomplexation, establishes the absolute configuration of Winterstein's acid 3-dimethylamino-3-phenyl propionic acid derived from Taxine B, as R.