On the racemisation of aspartic anhydride during its preparation

Frédéric Buron (1) , Geoffrey Deguest (2) , Laurent Bischoff (2) , Corinne Fruit (2) , Francis Marsais (3)

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

Due to the possible differentiation of both carboxyl groups, N-protected aspartic anhydride is a useful starting material in synthesis. However, most methods published in the literature for its formation lead to partial racemisation, which is generally not mentioned. Herein we report a comparison between the main methods published, with accurate measurements of the enantiomeric purity of this compound.

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

Frédéric Buron, Geoffrey Deguest, Laurent Bischoff, Corinne Fruit, Francis Marsais. On the racemisation of aspartic anhydride during its preparation. Tetrahedron: Asymmetry, 2007, 18 (13), pp.1625-1627. ⟨10.1016/j.tetasy.2007.07.003⟩. ⟨hal-02385023⟩