189562-57-0Relevant academic research and scientific papers
Remarkable diastereomeric rearrangement of an α-acyloxy β-ketosulfide to an α-acyloxy thioester: A novel approach to the synthesis of optically active (2S,3S) β-amino α-hydroxy acids
Suzuki, Takayuki,Honda, Yutaka,Izawa, Kunisuke,Williams, Robert M.
, p. 7317 - 7323 (2005)
A novel and efficient synthetic method is described for (2S,3S)-3-amino-2-hydroxy-4-phenyl butyric acid derivatives, which are useful intermediates of enzyme inhibitors. This involves a Pummerer rearrangement of a β-ketosulfoxide derived from L-phenylalanine followed by highly stereoselective acyl migration. From these studies, it appears that nitrogen-protecting groups exert a substantial influence over stereoselectivity. The mechanism of the rearrangement is discussed. β-Amino α-hydroxy carboxylic acids are important pharmaceutical intermediates, and this method may provide a versatile synthesis from various amino acids in a few steps.
