189013-27-2Relevant academic research and scientific papers
Asymmetric synthesis of (R)- and (S)-piperidin-2-yl-phosphonic acid by diastereoselective addition of trialkyl phosphite onto potential iminium salt
Maury, Catherine,Wang, Qian,Gharbaoui, Tawfik,Chiadmi, Mohamed,Tomas, Alain,Royer, Jacques,Husson, Henri-Philippe
, p. 3627 - 3636 (2007/10/03)
Two strategies have been developed to synthesize both enantiomers of piperidin-2-yl-phosphonic acid. The first one uses the double condensation of glutaraldehyde with (R)-(-)-phenylglycinol and triethylphosphite to give 2-ethylphosphonate-6-oxazolopiperidine 2 which furnished in few steps (S)-(+)-)piperidin-2yl-phosphonic acid (5) in 58% ee. The second strategy utilizes the 2-cyano-6-oxazolapiperidine synthon 1 which upon treatment with trimethyl phosphite gave 2-cyano-6-oxazaphosphorinane 7 which gave pure (R)-(-)-piperidin-2-yl-phosphonic acid (10) in good overall yield.
