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  • Title: Asymmetric synthesis of trans-3,4-dialkyl-gamma-butyrolactones via an acyl-Claisen and iodolactonization route.
    Author: Xu Q, Rozners E.
    Journal: Org Lett; 2005 Jul 07; 7(14):2821-4. PubMed ID: 15987145.
    Abstract:
    [reaction: see text] A new, efficient, and general asymmetric synthesis of enantiomerically pure trans-3,4-dialkyl-gamma-lactones has been developed. The key steps are (1) copper-catalyzed three-component coupling of chiral amine, aldehyde, and alkyne, (2) acyl-Claisen rearrangement, and (3) iodolactonization. The products, chiral gamma-lactones, are versatile synthetic intermediates and structural units of natural products and modified nucleosides.
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