Regioselective opening of N-Cbz glutamic and aspartic anhydrides with carbon nucleophiles

Geoffrey Deguest (1) , Laurent Bischoff (2) , Corinne Fruit (2) , Francis Marsais (1)

1 IRCOF - Institut de Chimie Organique Fine
2 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

Depending on the experimental conditions, aspartic and glutamic anhydrides can be opened regioselectively with Grignard reagents, thus giving access to different isomers of chiral amino-ketoesters.

Domains: Chemical Sciences; Chemical Sciences; Organic chemistry; Chemical Sciences; Medicinal Chemistry; Chemical Sciences; Radiochemistry; Chemical Sciences; Material chemistry; Chemical Sciences; Inorganic chemistry; Chemical Sciences; Catalysis

Geoffrey Deguest, Laurent Bischoff, Corinne Fruit, Francis Marsais. Regioselective opening of N-Cbz glutamic and aspartic anhydrides with carbon nucleophiles. Tetrahedron: Asymmetry, 2006, 17 (14), pp.2120-2125. ⟨10.1016/j.tetasy.2006.07.039⟩. ⟨hal-02385048⟩