2-(Ethoxycarbonylmethyl)-1H-naphtho[1,8-de]-1,2,3-triazine anion: a new glycine enolate equivalent

The titled triazine can be alkylated with LDA and a variety of alkyl halides: subsequent reduction with aluminium amalgam cleaves the naphthotriazine moiety to afford substituted α amino acids in excellent overall yields; the sequence defines a novel methodology that can be applied under non-acidic and largely non-aqueous conditions.