219
Views
5
CrossRef citations to date
0
Altmetric
Original Articles

Hydroxyphosphinylacetic acid as a chiral auxiliary compound

Pages 585-590 | Received 30 Sep 2018, Accepted 06 Nov 2018, Published online: 18 Dec 2018

References

  • Lin, G.-Q.; Li, Y.-M.; Chan, A. S. C. Principles and Applications of Asymmetric Synthesis; John Wiley: Chichester, 2001.; pp 1–7.
  • Seco, J. M.; Quinoa, E.; Riguera, R. The Assignment of Absolute Configuration by NMR. Chem. Rev. 2004, 104, 17–117.
  • Parker, D. NMR Determination of Enantiomeric Purity. Chem. Rev. 1991, 91, 1441–1457.
  • Blazewska, K. M.; Gajda, T. Assignment of the Absolute Configuration of Hydroxy- and Aminophosphonates by NMR Spectroscopy. Tetrahedron: Asymmetry. 2009, 20, 1337–1361.
  • Wenzel, T. J.; Wilcox, J. D. Chiral Reagents for the Determination of Enantiomeric Excess and Absolute Configuration Using NMR Spectroscopy. Chirality. 2003, 15, 256–270.
  • Hulst, R.; Kellogg, R. M.; Feringa, B. L. New Methodologies for Enantiomeric Excess (ee) Determination Based on Phosphorus NMR. Recl. Trav. Chim. Pays-Bas. 2010, 114, 115–138.
  • Szyszkowiak, J.; Majewska, P. Determination of Absolute Configuration by 31P NMR. Tetrahedron: Asymmetry. 2014, 25, 103–112.
  • Majewska, P.; Kafarski, P.; Lejczak, B.; Bryndal, I.; Lis, T. An Approach to the Synthesis and Assignment of the Absolute Configuration of All Enantiomers of Ethyl Hydroxy(phenyl)Methane(P-Phenyl)Phosphinate. Tetrahedron: Asymmetry. 2006, 17, 2697–2701.
  • Majewska, P.; Kafarski, P.; Lejczak, B. Simple and Effective Method for the Deracemization of Ethyl 1-Hydroxyphosphinate Using Biocatalysts with Lipolytic Activity. Tetrahedron: Asymmetry. 2006, 17, 2870–2875.
  • Majewska, P.; Doskocz, M.; Lejczak, B.; Kafarski, P. Enzymatic Resolution of α-Hydroxyphosphinates with Two Stereogenic Centres and Determination of Absolute Configuration of Stereoisomers Obtained. Tetrahedron: Asymmetry. 2009, 20, 1568–1574.
  • Majewska, P. Biotransformations of 2-Hydroxy-2-(Ethoxyphenylphosphinyl)Acetic Acid and the Determination of the Absolute Configuration of All Isomers. Bioorg. Chem. 2015, 61, 28–35.
  • Szakács, Z.; Sánta, Z.; Lomoschitz, A.; Szántay, C., Jr. Self-Induced Recognition of Enantiomers (SIRE) and Its Application in Chiral NMR Analysis. Trends Anal. Chem. 2018, 109, 180–197.
  • Kozlowski, J. K.; Rath, N. P.; Spilling, C. D. Determination of the Enantiomeric Purity and Absolute Configuration of α-Hydroxy Phosphonates. Tetrahedron. 1995, 51, 6385–6396.
  • Rojas-Cabrera, H.; Fernandez-Zertuche, M.; Garcia-Barradas, O.; Munoz-Muniz, O.; Ordonez, M. Preparation of Dimethyl (R)- and (S)-2-(2-Hydroxyphenyl)-2-Hydroxyethylphosphonate Derived from Salicylaldehyde via Resolution Using (S)-Methoxyphenylacetic Acid (MPA). Tetrahedron: Asymmetry. 2007, 18, 142–148.
  • Majewska, P.; Serafin, M.; Klimek-Ochab, M.; Brzezińska-Rodak, M.; Żymańczyk-Duda, E. Lipases and Whole Cell Biotransformations of 2-Hydroxy-2-(Ethoxyphenylphosphinyl)Acetic Acid and Its Ester. Bioorg. Chem. 2016, 66, 21–26.
  • Webb, R. G.; Haskell, M. W.; Stammer, C. H. A Nuclear Magnetic Resonance Method for Distinguishing α-Amino Acids from β and γ Isomers. J. Org. Chem. 1969, 34, 576–580.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.