Tertiary Aromatic Amide for Memory of Chirality: Access to Enantioenriched α-Substituted Valine
M Branca, D Gori, R Guillot, V Alezra…
Index: Branca, Mathieu; Gori, Didier; Guillot, Regis; Alezra, Valerie; Kouklovsky, Cyrille Journal of the American Chemical Society, 2008 , vol. 130, # 18 p. 5864 - 5865
Full Text: HTML
Citation Number: 27
Abstract
A new methodology for the asymmetric synthesis of quaternary α-substituted amino acids using memory of chirality has been developed. This strategy employs dynamic axial chirality of tertiary aromatic amides to memorize the initial chirality of an α-amino acid during the enolization step. Starting from l-valine, an oxazolidin-5-one containing a tertiary aromatic amide was synthesized in one step and then alkylated with various electrophiles with ...
Related Articles:
[Branca, Mathieu; Pena, Sebastien; Guillot, Regis; Gori, Didier; Alezra, Valerie; Kouklovsky, Cyrille Journal of the American Chemical Society, 2009 , vol. 131, # 30 p. 10711 - 10718]
[Seebach, Dieter; Aebi, Johannes D.; Naef, Reto; Weber, Theodor Helvetica Chimica Acta, 1985 , vol. 68, p. 144 - 154]
Enzymatic resolution of α, α-disubstituted α-amino acid esters and amides
[Kaptein; Boesten; Broxterman; Peters; Schoemaker; Kamphuis Tetrahedron Asymmetry, 1993 , vol. 4, # 6 p. 1113 - 1116]
[Seebach, Dieter; Aebi, Johannes D.; Naef, Reto; Weber, Theodor Helvetica Chimica Acta, 1985 , vol. 68, p. 144 - 154]