Diastereoselective Synthesis of Anti‐β‐Substituted α‐Aminobutanoic Acids via Michael Addition Reactions of Nucleophiles to New Chiral Ni(II) Complexes of Dehydroaminobutanoic Acid

Abstract

New chiral Ni^II complex of the dehydroaminobutanoic acid Schiff base with (S)‐N‐(2‐benzoylphenyl)‐1‐(3,4‐dichlorbenzyl)pyrrolidyl‐2‐carboxamide (CPB) was synthesized and tested as electrophile component in the asymmetric Michael addition reactions with nucleophiles (imidazole, benzylamine, methoxy ion, ethoxy ion). The method of the asymmetric synthesis of β‐substituted (S)‐α‐amino acids with high d.e > 80% was developed.

Keywords:

• Diastereoselective synthesis
• chiral Ni^II complex
• β‐substituted (S)‐α‐amino acids

Acknowledgments

The authors are grateful to Prof. Yu.N. Belokon' for fruitful discussion during the preparation of the manuscript. The research described was supported by the ISTC grant 2780.