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Samarium Iodide-Mediated Reformatsky Reactions for the Stereoselective Preparation of beta-Hydroxy-gamma-amino Acids: Synthesis of Isostatine and Dolaisoleucine

  1. Author:
    Nelson, C. G.
    Burke, T. R.

  2. Author Address

    [Nelson, Christopher G.; Burke, Terrence R., Jr.] NCI, Biol Chem Lab, Mol Discovery Program, Ctr Canc Res,NIH, Frederick, MD 21702 USA.;Burke, TR (reprint author), NCI, Biol Chem Lab, Mol Discovery Program, Ctr Canc Res,NIH, Frederick, MD 21702 USA;tburke@helix.nih.gov
    1. Year: 2012
    2. Date: Jan
  2. Journal: Journal of Organic Chemistry
    1. 77
    2. 1
    3. Pages: 733-738
  4. Type of Article: Article
  5. ISSN: 0022-3263
  1. Abstract:

    The synthesis of beta-hydroxy-gamma-amino acids via SmI(2)-mediated Reformatsky reactions of alpha-chloroacetyloxazolidinones with aminoaldehydes is reported. Diastereoselective coupling is demonstrated to depend on the absolute configuration of the Evans chiral auxiliary employed in the reaction, allowing egthro or threo products to be obtained selectively. The potential utility of the methodology is exemplified by the facile synthesis of biologically relevant N-Boc-isostatine (2b) and N-Boc-dolaisoleucine (3c).

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External Sources

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  2. DOI: 10.1021/jo202091r
  3. View record in Web of Science®
  4. WOS: 000298827600078

Library Notes

  1. Fiscal Year: FY2011-2012
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