Journal article

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

Reaction of N,N-dibenzyl-O-methylsulfonyl serine Me 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. [on SciFinder (R)]


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