188241-79-4Relevant academic research and scientific papers
An enantioselective, stereodivergent synthesis of threonine analogs
Delle Monache, Giuliano,Di Giovanni, Maria Cristina,Misiti, Domenico,Zappia, Giovanni
, p. 231 - 243 (2007/10/03)
An enantioselective and stereodivergent methedology for the synthesis of the four isomers of P-hydroxy norvaline is presented starting from the common oxazolidin-2-one intermediate 1, via an iterative formation of the oxazolidin-2-one ring to achieve the stereochemical control of the stereogenic centers. The flexibility of the present approach, for the synthesis of several threonine analogs, lies in the ready displacement of the sulfonate group in 2 with the Grignard reagents in the presence of CuI.
Chiral 4,5-Disubstituted Oxazolidin-2-ones: Stereoselective Synthesis of β-Hydroxy-α-amino Acids
Giovanni, Maria Cristina Di,Misiti, Domenico,Zappia, Giovanni,Monache, Giuliano Delle
, p. 475 - 482 (2007/10/03)
The stereocontrolled synthesis of β-hydroxy-α-amino acids from O-benzyl D- and L-serine, by the use of 4,5-disubstituted oxazolidin-2-ones as chiral intermediates, is presented as a suitable alternative to the known procedures.The reported synthesis of both enantiomers of threo-3-hydroxyglutamic acid and (2S,3R)-3-hydroxyproline together with a flexible and stereodivergent preparation of threonine analogues is discussed as an example of the versatility of the present approach.
