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  • Title: Organocatalytic asymmetric Michael addition of 5H-oxazol-4-ones to nitroolefins.
    Author: Qiao B, An Y, Liu Q, Yang W, Liu H, Shen J, Yan L, Jiang Z.
    Journal: Org Lett; 2013 May 17; 15(10):2358-61. PubMed ID: 23642091.
    Abstract:
    The first organocatalytic asymmetric Michael addition of 5H-oxazol-4-ones to nitroolefins has been developed. In the presence of easily prepared L-tert-leucine-derived tertiary amine/thiourea catalyst, the Michael addition of 5H-oxazol-4-ones to nitroolefins proceeded in an excellent diastereo- and enantioselective manner (up to 99% ee and >19:1 dr). The Michael adducts obtained are valuable precursors for the synthesis of chiral α-alkyl-α-hydroxy carboxylic acid derivatives, which represent a series of versatile building blocks in many biologically active compounds.
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