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  • Title: Three component coupling of alpha-iminoesters via umpolung addition of organometals: synthesis of alpha,alpha-disubstituted alpha-amino acids.
    Author: Dickstein JS, Fennie MW, Norman AL, Paulose BJ, Kozlowski MC.
    Journal: J Am Chem Soc; 2008 Nov 26; 130(47):15794-5. PubMed ID: 18983153.
    Abstract:
    The synthesis of alpha,alpha-disubstituted alpha-amino acids by means of a three component coupling is reported. The coupling occurs through umpolung addition of organometallic reagents to the nitrogen of alpha-iminoesters. The resulting enolate intermediates subsequently react with electrophiles (aldehydes, imines, alpha,beta-unsaturated nitro, alkyl halides, acyl cyanides) to form a quaternary center. Tethering of the electrophile and nucleophile components provides cyclic alpha,alpha-disubstituted alpha-amino acid derivatives.
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