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  • Title: Efficient synthesis of chiral beta-seleno amides via ring-opening reaction of 2-oxazolines and their application in the palladium-catalyzed asymmetric allylic alkylation.
    Author: Braga AL, Vargas F, Sehnem JA, Braga RC.
    Journal: J Org Chem; 2005 Oct 28; 70(22):9021-4. PubMed ID: 16238343.
    Abstract:
    [structure: see text] A set of chiral beta-seleno amides have been efficiently synthesized via the ring-opening reaction of chiral 2-oxazolines by selenium nucleophiles. The present method is applicable to the synthesis of beta-seleno amides containing thioether, alcohol, and ether moieties in good yields. As an application, the synthesis of a selenocysteine derivative has been accomplished. Additionally, these new compounds were evaluated in the palladium-catalyzed asymmetric allylic alkylation, giving the alkylated products in up to 98% ee.
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