Towards Convenient Precursors for α -Phosphonylated Aziridinium Ions

Abstract

Mixtures of the respective 2-(N,N-dibenzylamino)-1-chloro- and 1-(N,N-dibenzylamino)-2-chlorophosphonates were obtained after mesylation of dimethyl (1R,2S)-2-(N,N-dibenzylamino)-1-hydroxy-3-methylbutylphosphonate and diethyl (1R,2S)-2-(N,N-dibenzylamino)-1-hydroxy-3-phenylpropylphosphonate with mesyl chloride in the presence of tetraethylammonium chloride. These mixtures are considered as useful precursors to α -phosphonylated aziridinium ions.

Keywords:

• 2-Amino-1-hydroxyphosphonates
• aziridinium ions
• 1-chlorophosphonates
• 2-chlorophosphonates
• regioselectivity

Dedicated to Professor Marian Mikołajczyk from the CBMiM PAN in Łódź, Poland, on the occasion of his 70th birthday.

We thank the Medical University of Łódź for financial support under internal grant 503-3014-1 and Mrs. Jolanta Płocka for excellent technical assistance.