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...

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Bibliographic Details
Published in:Organic letters 2014-02, Vol.16 (3), p.788-791
Main Authors: Viswambharan, Baby, Gori, Didier, Guillot, Régis, Kouklovsky, Cyrille, Alezra, Valérie
Format: Article
Language:English
Subjects:
Alanine - chemistry
Aldehydes - chemistry
Amides - chemistry
Amino Acids - chemistry
Catalysis
Molecular Structure
Stereoisomerism
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol403523e