Chemistry - A European Journal p. 5787 - 5798 (2017)
Update date:2022-09-26
Topics:
Mai, Thi Thoa
Viswambharan, Baby
Gori, Didier
Guillot, Régis
Naubron, Jean-Valère
Kouklovsky, Cyrille
Alezra, Valérie
One of the fundamental and intriguing aspects of life is the homochirality of the essential molecules. In this field, the absolute asymmetric synthesis of α-amino acids is a major challenge. Herein, we report access, by chemical means, to tertiary α-amino acid derivatives in up to 96 % ee without using any chiral reagent. In our strategy, the dynamic axial chirality of tertiary aromatic amides is frozen in a crystal and is responsible for the stereoselectivity of the subsequent steps. Furthermore, we could control the configuration of the final product by manually sorting and selecting the initial crystals. Based on vibrational circular dichroism studies, we could rationalize the observed stereoselectivity.
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