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Organocatalytic Asymmetric Michael Addition of 5H‑Oxazol-4-ones to Nitroolefins

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journal contribution
posted on 17.05.2013, 00:00 by Baokun Qiao, Yongqiang An, Qian Liu, Wenguo Yang, Hongjun Liu, Juan Shen, Lin Yan, Zhiyong Jiang
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.