Aziridinium from N,N-Dibenzyl Serine
Methyl Ester:  Synthesis of
Enantiomerically Pure β-Amino and
α,β-Diamino Esters

Zhu, Jieping

Aziridinium from N,N-Dibenzyl Serine Methyl Ester: Synthesis of Enantiomerically Pure β-Amino and α,β-Diamino Esters

Posted on 2006-05-11 - 00:00

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 β-amino or α,β-diamino ester in good to excellent yield. A short synthesis of orthogonally protected and enantiomerically pure 2,3-diamino propionate (Dap) is described.

CITE THIS COLLECTION

Couturier, Cédric; Blanchet, Jérome; Schlama, Thierry; Zhu, Jieping (2016). Aziridinium from N,N-Dibenzyl Serine Methyl Ester: Synthesis of Enantiomerically Pure β-Amino and α,β-Diamino Esters. ACS Publications. Collection. https://doi.org/10.1021/ol060700u

https://doi.org/10.1021/ol060700u

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