Absolute Asymmetric Synthesis of Tertiary α-Amino Acids


  • We thank the Ministère de la Recherche et de l’enseignement supérieur (doctoral grant to M.B.) and the ANR (Agence Nationale de la Recherche; ANR grant n°ANR-08-JCJC0099, doctoral grant to T.T.M.) for financial support. The authors thank Dr. David Berardan (ICMMO) for assistance and loan of planetary ball mill and Dr. Susannah Coote for assistance with the English-language editing of the manuscript.


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Frozen: The spontaneous crystallization of an achiral compound in a chiral conformation is used as the unique source of chirality in an absolute asymmetric synthesis of tertiary amino acids. The dynamic axial chirality of tertiary aromatic amides is frozen in a crystal (see picture) and is responsible for the stereoselectivity of the deprotonation/alkylation (see scheme). α-Amino acid derivatives are synthesized in up to 96 % ee.