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  • Title: Diastereoselective synthesis of alpha-methyl and alpha-hydroxy-beta-amino acids via 4-substituted-1,3-oxazinan-6-ones.
    Author: Sleebs BE, Hughes AB.
    Journal: J Org Chem; 2007 Apr 27; 72(9):3340-52. PubMed ID: 17402786.
    Abstract:
    1,3-oxazinan-6-ones have been utilized in a series of enolate reactions to produce 5-hydroxy and 5-alkyl-4-substituted-1,3-oxazinan-6-ones with excellent trans diastereoselectivity. Highlighting the versatility of the oxazinanone, a number of transformations were performed to produce a variety of protected N-H and N-methyl alpha-hydroxy- and alpha-methyl-beta-amino acids.
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