ASYMMETRIC-SYNTHESIS OF (R)-PIPERIDIN-2-YL-PHOSPHONIC AND (S)-PIPERIDIN-2-YL-PHOSPHONIC ACID BY DIASTEREOSELECTIVE ADDITION OF TRIALKYL PHOSPHITE ONTO POTENTIAL IMINIUM SALT

Authors
MAURY C WANG Q GHARBAOUI T CHIADMI M TOMAS A ROYER J HUSSON HP
Citation
C. Maury et al., ASYMMETRIC-SYNTHESIS OF (R)-PIPERIDIN-2-YL-PHOSPHONIC AND (S)-PIPERIDIN-2-YL-PHOSPHONIC ACID BY DIASTEREOSELECTIVE ADDITION OF TRIALKYL PHOSPHITE ONTO POTENTIAL IMINIUM SALT, Tetrahedron, 53(10), 1997, pp. 3627-3636
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
10
Year of publication
1997
Pages
3627 - 3636
Database
ISI
SICI code
0040-4020(1997)53:10<3627:AO(A(>2.0.ZU;2-S
Abstract
Two strategies have been developed to synthesize both enantiomers of, piperidin-2-yl-phosphonic acid The first one uses the double condensat ion of glutaraldehyde with (R)-(-)-phenylglycinol and; triethylphosphi te to give 2-ethylphosphonate-6-oxazolopiperidine 2 which furnished in few steps (S)-(+)-piperidin-2yl-phosphonic acid (5) in 58% ee. The se cond strategy utilizes the 2-cyano-6-oxazolopiperidine synthon 1 which upon treatment with trimethyl phosphite gave 2-cyano-6-oxazaphosphori nane 7 which gave pure (R)-(-)-piperidin-2-yl-phosphonic acid (10) in good overall yield. (C) 1997 Elsevier Science Ltd.