188965-46-0Relevant academic research and scientific papers
Tunable Stereoselectivity in the Addition of 2-Lithiothiazole to L-Serinal Derived N-Benzyl Nitrone. Synthesis of C-2 Epimer 2,3-Diamino-4-Hydroxybutanals
Dondoni, Alessandro,Merchan, Francisco L.,Merino, Pedro,Tejero, Tomas,Bertolasi, Valerio
, p. 1731 - 1734 (1994)
A complete reversal of diastereoselectivity (ds 95percent) in the addition of 2-lithiothiazole to L-serinal derived N-benzyl nitrone has been achieved by the change of the hydroxy and amino protective groups in the aldehyde moiety; the resultant epime
Totally stereocontrolled synthesis of α,β-diamino acids by addition of grignard reagents to nitrones derived from L-serine
Merino, Pedro,Lanaspa, Ana,Merchan, Francisco L.,Tejero, Tomas
, p. 629 - 646 (2007/10/03)
The asymmetric synthesis of protected (2R,3S)- and (2R,3R)-3-substituted 2,3-α-amino acids is reported. The key step in the synthesis of these compounds is the diastereoselective addition of Grignard reagents to α- amino nitrones derived from L-serine. Total stereocontrol of the addition step is achieved by changing the protecting groups in the starting material. The predominant selectivity in each case can be reasonably interpreted in terms of steric effects of the substituents.
