89105-35-1Relevant academic research and scientific papers
2-(Ethoxycarbonylmethyl)-1H-naphtho[1,8-de]-1,2,3-triazine anion: A new glycine enolate equivalent
Anilkumar,Chandrasekhar,Sridhar
, p. 6665 - 6668 (2007/10/03)
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. (C) 2000 Elsevier Science Ltd.
(3R)- AND (3S)-METHYLPIPERAZINE-2,5-DIONE DERIVATIVES AS USEFUL INTERMEDIATES IN THE ENANTIOSELECTIVE SYNTHESIS OF α-AMINO ESTERS
Orena, Mario,Porzi, Gianni,Sandri, Sergio
, p. 2125 - 2152 (2007/10/02)
Treatment of (3S)-3-methylpiperazine-2,5-dione 1 with lithium hexamethyldisilazide (LHMDS) followed by alkylation with several alkyl bromides affords (3S,6S)-3-methyl-6-alkyl derivatives 3 (a-e) in d.e. greater than 98percent.The same reaction sequence carried out on the (3R)-derivative 2 leads to a diastereoisomeric mixture of (3R,6S)-4 (a-e) and (3R,6R)-5 (a-e), the ratio 5 : 4 depending on the alkylating reagent.The configuration at C-6 (of 3, 4 and 5) has been assigned on the basis of 1H-NMR spectroscopic data and conformational analysis performed by the MMPMI program.Cleavage of the heterocyclic ring of 3 (b, d) and 5 (b, d) leads to the corresponding (S)- and (R)-α-amino esters respectively.
