Asymmetric Synthesis of Anti N -Boc-α-Hydrazino-β-Hydroxyesters from β-Ketoesters by Sequential Catalytic Hydrogenation and Electrophilic Amination

Christine Greck (1) , Laurent Bischoff (2) , Franck Ferreira (3) , Catherine Pinel (4) , Eric Piveteau , Jean Pierre Genêt (5)

1 ILV - Institut Lavoisier de Versailles
2 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
3 ROCS - Réactivité organométallique et catalyse pour la synthèse
4 IRCELYON - Institut de recherches sur la catalyse et l'environnement de Lyon
5 ENSCP - Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL

Enantiomerically pure anti N-Boc-α-hydrazino-β-hydroxyesters were obtained from the corresponding β-ketoesters by hydrogenation with chiral Ruthenium catalysts and electrophilic amination of the β-hydroxyester with di-tert-butylazodicarboxylate (DBAD).

Domaines: Chimie; Chimie organique; Chimie thérapeutique; Radiochimie; Matériaux; Chimie inorganique; Catalyse

Christine Greck, Laurent Bischoff, Franck Ferreira, Catherine Pinel, Eric Piveteau, et al.. Asymmetric Synthesis of Anti N -Boc-α-Hydrazino-β-Hydroxyesters from β-Ketoesters by Sequential Catalytic Hydrogenation and Electrophilic Amination. SYNLETT, 1993, 1993 (07), pp.475-477. ⟨10.1055/s-1993-22496⟩. ⟨hal-02385501⟩