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A Highly Enantioselective Route to Either Enantiomer of Both α- and β-Amino Acid Derivatives | Journal of the American Chemical Society
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    A Highly Enantioselective Route to Either Enantiomer of Both α- and β-Amino Acid Derivatives
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    The Skaggs Institute for Chemical Biology and the Department of Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037
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    Cite this: J. Am. Chem. Soc. 2002, 124, 9, 1866–1867
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    https://doi.org/10.1021/ja017833p
    Published February 8, 2002
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    This report describes the unprecedented use of unmodified aldehydes as donors in a catalytic asymmetric Mannich-type reaction. The proline-catalyzed reaction of N-PMP-protected α-imino ethyl glyoxylate with unmodified aliphatic aldehydes provided a general and very mild entry to either enantiomer of β-amino and α-amino acids and derivatives in high yield and stereoselectivity. Six of the seven aldehydes studied yielded products with ee values of 99% or greater. The diastereoselectivity of the reaction increased with the bulkiness of the substituents of the aldehyde donor in the order R = Me < Et < i-Pr < n-Pent. In five of the cases studied, excellent syn stereoselectivities were achieved. In addition, the corresponding chiral β-amino aldehyde adducts can be readily converted to the corresponding amino acid derivatives. Most significantly, this approach provides facile access to substituted β-lactams.

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    Cite this: J. Am. Chem. Soc. 2002, 124, 9, 1866–1867
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