Substrate Control in Enantioselective and Diastereoselective Aldol Reaction by Memory of Chirality: A Rapid Access to Enantiopure β‑Hydroxy Quaternary α‑Amino Acids

An
asymmetric aldol reaction by memory of chirality is reported
with a substrate control of stereoselectivity by aldehyde and rationalized.
Starting from l-alanine, several diastereo­pure and
enantio­enriched β-hydroxy quaternary α-amino acids
have been obtained in three steps. The initial chirality of l-alanine is memorized through the dynamic axial chirality of tertiary
aromatic amide.