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

Cédric Couturier; Jérome Blanchet; Thierry Schlama; Jieping Zhu

doi:10.1021/ol060700u

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

Org Lett. 2006 May 11;8(10):2183-6. doi: 10.1021/ol060700u.

Authors

Cédric Couturier¹, Jérome Blanchet, Thierry Schlama, Jieping Zhu

Affiliation

¹ Institut de Chimie des Substances Naturelles, CNRS, Gif-sur-Yvette, France.

PMID: 16671812
DOI: 10.1021/ol060700u

Abstract

[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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aziridines / chemical synthesis*
Esters
Molecular Structure
Propionates / chemical synthesis*
Serine / analogs & derivatives*
Serine / chemistry
Stereoisomerism

Substances

Aziridines
Esters
N,N-dibenzyl aziridinium-2-carboxylate
Propionates
Serine
serine methyl ester