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  • Aziridinium from N,N-dibenzyl serine methyl ester: synthesis of enantiomerically pure beta-amino and alpha,beta-diamino esters.

Aziridinium from N,N-dibenzyl serine methyl ester: synthesis of enantiomerically pure beta-amino and alpha,beta-diamino esters.

Organic letters (2006-05-05)
Cédric Couturier, Jérome Blanchet, Thierry Schlama, Jieping Zhu
ZUSAMMENFASSUNG

[reaction: see text] Reaction of N,N-dibenzyl-O-methylsulfonyl serine methyl ester with a variety of heteronucleophiles (sodium azide, sodium phthalimide, amines, thiols) and carbanions (sodium malonate) gave, via an aziridinium intermediate, the corresponding beta-amino or alpha,beta-diamino ester in good to excellent yield. A short synthesis of orthogonally protected and enantiomerically pure 2,3-diamino propionate (Dap) is described.

MATERIALIEN
Produktnummer
Marke
Produktbeschreibung

Sigma-Aldrich
L-Serinmethylester -hydrochlorid, 98%
Sigma-Aldrich
D-Serinmethylester -hydrochlorid, 98%
Sigma-Aldrich
DL-Serin-methylester -hydrochlorid, 98%