178601-75-7Relevant academic research and scientific papers
Neighbouring group effects promote substitution reactions over elimination and provide a stereocontrolled route to chloramphenicol
Easton, Christopher J.,Hutton, Craig A.,Merrett, Martin C.,Tiekink, Edward R. T.
, p. 7025 - 7036 (2007/10/03)
In reactions of β-brominated valine and p-nitrophenylalanine derivatives to give β-hydroxy amino acid derivatives the carboxyl group, when protected as an amide, exerts a neighbouring group effect to facilitate the substitution process, and reduce competing elimination reactions. As a consequence of the effect, the (2R,3R)- and (2R,3S)-stereoisomers of 3-bromo-N-tert-butyl-N(α)-phthaloyl-p-nitrophenylalaninamide both react to give (2S,3R)-3-hydroxy-N-tert-butyl-N(α)-phthaloyl-p-nitrophenylalaninamid e, providing a stereoconvergent route to chloramphenicol.
