Straightforward Synthesis of 1,2-Amino Phosphate Diesters and Application to the Synthesis of Novel 1,2-Amino Ether Diesters

Abstract

A variety of 1,2-amino alcohol diesters 1 reacted smoothly with diethyl chlorophosphate under basic conditions to afford the corresponding 1,2-amino phosphate diesters 2 in excellent yields. These compounds served as useful precursors for subsequent nucleophilic attack by alcohols in an S_N2 fashion to provide 1,2-amino ether diesters 3.

Keywords:

• 1,2-Amino alcohol diesters
• 1,2-amino ether diesters
• 1,2-amino phosphate diesters
• diethyl chlorophosphate

ACKNOWLEDGMENTS

We thank Prof. M. Bellassouad (Université Cergy-Pontoise) for providing microanalysis and Prof. M. Chaabouni (ESIAT) for helpful discussions.

Notes

^a Compounds were mixtures of two diastereomers (α + β) (entries 2–6) derived from the 1:1 mixture of 1.

^b Yields refer to isolated chromatographically pure compounds.

^a Compounds 3 were mixtures of two diastereomers (α + β) (entries 2–8) derived from the 1:1 mixture of 2.

^b Yields refer to isolated chromatographically pure compounds.