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Asymmetric Nucleophilic Glyoxylation through a Metalated α-Aminonitrile Derivative in Michael Additions to Nitroalkenes


  • This work was supported by the Fonds der Chemischen Industrie. We thank Boehringer Mannheim GmbH, BASF AG, and Bayer AG for the donation of chemicals. The collection of the X-ray data by Dr. C. W. Lehmann, MPI Mülheim, is gratefully acknowledged.


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Efficient and selective: An asymmetric nucleophilic glyoxylation has been achieved for the first time using a metalated glyoxylate aminonitrile derivative in Michael additions to nitroalkenes. After conversion of the aminonitrile back into the keto function with removal of the chiral auxiliary, the γ-nitro α-keto esters were available in good yields and excellent enantiomeric excesses (see scheme).

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