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  • Title: Asymmetric Michael addition of malonates to enones catalyzed by a primary β-amino acid and its lithium salt.
    Author: Yoshida M, Narita M, Hara S.
    Journal: J Org Chem; 2011 Oct 21; 76(20):8513-7. PubMed ID: 21894973.
    Abstract:
    Highly enantioselective Michael addition of malonates to enones was achieved using a mixed catalyst consisting of a primary β-amino acid, O-TBDPS (S)-β-homoserine, and its lithium salt. Various cyclic and acyclic enones were converted into 1,5-ketoesters in high yields (up to 92%) with high enantioselectivity (up to 97% ee) under mild reaction conditions. Details of synthesis of the catalyst, optimization of the reaction conditions for the Michael addition reaction, and a plausible reaction mechanism are described.
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