Amino Phosphate Monoesters: A Convenient Source of 2-Alkylamino-3-methoxy-3-phenylpropionates via Aziridinium Ions

Abstract

The synthesis of a series of amino ethers was carried out in a two-step method involving phosphorylation of the corresponding amino alcohols and subsequent double displacement via an aziridinium intermediate. The new products were obtained in good yields with excellent regioselectivity.

GRAPHICAL ABSTRACT

Keywords:

• 1,2-Amino alcohol monoesters
• 1,2-amino phosphate monoesters
• 1,2-amino ether monoesters
• aziridinium ions

ACKNOWLEDGMENT

We thank M. A. Sanhoury, member of the Royal Society of Chemistry (MRSC) of the Department of Chemistry, Faculty of Sciences of Tunis, for helpful discussions.

Notes

^a 4b and c were 1:1 mixtures of two diastereomers (α + β) derived from the 1:1 mixture of 3b and c.

^b Yields refer to chromatographically isolated pure compounds.

^a 5b and c were 1:1 mixtures of two diastereomers (α + β) derived from the 1:1 mixture of 4b and c.

^b Yields refer to chromatographically isolated pure compounds.