Chemical Resolution of <i>C</i>,<i>N</i>‑Unprotected α‑Substituted β‑Amino Acids Using Stable and Recyclable Proline-Derived Chiral Ligands
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We report the first purely chemical method for the resolution of C,N-unprotected racemic α-substituted β-amino acids (β2-AAs) using thermodynamically stable and recyclable chiral proline-derived ligands. The ligands and racemic β2-AAs along with Ni(II) could form a pair of Ni(II) complex diastereoisomers with a desirable diastereoselectivity (dr up to 91:9). Enantiomerically pure C,N-unprotected β2-AAs could be obtained by simple hydrolysis of an isolated favored Ni(II) complex. The method featured unique versatility compared with enzymatic approaches and characterized by its broad synthetic generality, good stereochemical outcome, and mild reaction conditions, thus making it a powerful supplement in the field of chemical resolution of β2-AAs.
