Chiral symmetric phosphoric acid esters as sources of optically active organophosphorus compounds

Tetrahedron Asymmetry

Volumn 9, Issue 10, 1998, Pages 1645-1649

  Kolodiazhnyi, Oleg I ^a   Grishkun, Evgen V ^a   Sheiko, Serge ^a   Demchuk, Oleg ^a   Thoennessen, Holger ^b   Jones, Peter G ^b   Schmutzler, Reinhard ^b  

^a INSTITUTE OF BIOORGANIC CHEMISTRY AND PETROCHEMISTRY   (Ukraine)

^b Inst Anorganische Analyt Chem T   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BORNEOL; MENTHOL; ORGANOPHOSPHORUS COMPOUND;

ARTICLE; CONFORMATIONAL TRANSITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032557627     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00166-9     Document Type: Article

References (19)

1. Kolodiazhnyi O. I. Tetrahedron: Asymmetry 1998, 9, 1279.
2. Valentine Jr. D. Asymmetric Synthesis; Morrison J. D., Scott J. W., Ed.; Academic Press: Orlando, San Diego, New York, 1984, Vol. 4, pp. 267-312.
3. (a) Tasz M. K., Gamliel A., Rodriguez O. P., Lane T. M., Cremer S. E., Bennett D. W. J. Org. Chem. 1995, 60, 6281.
4. (b) Blazis V. J., Koeller K. J., Spilling C. D. Tetrahedron: Asymmetry 1994, 5, 499.
5. (c) Rath P., Spilling C. D. Tetrahedron Lett. 1994, 35, 227.
6. (d) Sum V., Kee T. P. J. Chem. Soc., Perkin Trans. 1 1993, 1778.
7. (e) Sum V., Kee T. P. J. Chem. Soc., Perkin Trans. 1 1993, 2701.
8. (f) Warren S., Wyatt P. Tetrahedron: Asymmetry 1996, 7, 989.
9. (a) Patel D. V., Rielly-Gauvin D. E. Tetrahedron Lett. 1990, 31, 5587.
10. (b) Denmark S. E., Chatani N., Pansare S. V., Tetrahedron 1992, 48, 2191.
11. (c) Sikorski J. A., Miller M. J., Braccolino D. S., Cleary D. G., Corey S. D., Font J. L., Gruis K. J., Han C. Y., Lin K. C., Pansegrau P. D., Ream J. E., Schnur D., Shah A., Walker M. C. Phosphorus, Sulfur and Silicon 1993, 76, 115.
12. (d) Stowasser B., Budt K.-H., Jian-Qi L., Peyman A., Ruppert D. Tetrahedron Lett. 1992, 33, 6625.
13. (a) Hammerschmidt F., Völlenkle H. Liebigs Ann. Chem. 1989, 577.
14. (b) Yokomatsu T., Shibuia S. Tetrahedron: Asymmetry 1992, 3, 377.
15. (c) Maier L. Phosphorus, Sulfur and Silicon 1993, 76, 119.
16. (d) Kameani T., Kigasawa K., Hiragi M. Heterocycles 1981, 16, 1205.
17. Blazis V. J., Koeller K. J., Spilling C. D. J. Org. Chem. 1995, 60, 931.
18. D -24.5 (c 0.15, ethyl acetate). The preparations of compounds 2-7 will be described in detail: Kolodiazhnyi O. I., Grishkun E. V., Sheiko S., Demchuk O., Thoennessen H., Jones P., Schmutzler R. Russ. Chem. Bull., in press.
19. The NMR spectra were recorded on a Varian VXR-300MHz spectrometer. HPLC analyses were performed on a Milichrom-1A (Russia) Silasorb DEA column. Commercially available chiral alcohols (1R,2S,5R)-(-)-menthol, [(1S)-endo]-(-)-borneol and (-)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose of 98% enantiomeric purity were used in this work.