153805-45-9Relevant academic research and scientific papers
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.
A straightforward synthesis of (2S,3R)-3-hydroxyproline and trans-(2R,3S)-2-hydroxymethyl-3-hydroxypyrrolidine
Dell'Uomo, Natalina,Di Giovanni, Maria Cristina,Misiti, Domenico,Zappia, Giovanni,Delle Monache, Giuliano
, p. 181 - 188 (2007/10/03)
A stereocontrolled synthesis of (2S,3R)-3-hydroxyproline 1, and trans-(2R,3S)-2-hydroxymethyl-3-hydroxypyrrolidine 2 has been achieved in 21% and 38% yield via the homochiral 4,5-disubstituted oxazolidin-2-one 3. The trans relationship in 2 has been introduced by a modified Mitsunobu reaction.
A stereoselective synthesis of 3(R)-hydroxy-2(S)-ornithine
Di Giovanni, Maria C.,Misiti, Domenico,Zappia, Giovanni,Delle Monache, Giuliano
, p. 11321 - 11328 (2007/10/02)
(2S,3R) Threo-3-hydroxy-ornithine has been synthesized efficiently using a highly stereoselective iodocyclocarbamation of the chiral Z-olefin 7 prepared from D-serine.
