2-Chloro-(4R,5R)-bis[(1R,2S,5R)-menth-1-yloxycarbonyl]-1,3, 2-dioxaphospholane: A practical chiral pool-derived reagent for determining enantiomeric purity of alcohols

Journal of Organic Chemistry

Volumn 73, Issue 10, 2008, Pages 3907-3910

  Amberg, Matthias ^a   Bergsträsser, Uwe ^a   Stapf, Georg ^a   Hartung, Jens ^a  

^a Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRALITY; CHLORINE COMPOUNDS; CRYSTALLINE MATERIALS; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE;

CHIRAL ALCOHOLS; CRYSTALLINE SOLID; ENANTIOMERIC PURITY;

ALCOHOLS;

2 CHLOROBIS(MENTH 1 YLOXYCARBONYL) 1,3,2 DIOXAPHOSPHOLANE; ALCOHOL DERIVATIVE; REAGENT;

ARTICLE; CHEMICAL STRUCTURE; CRYSTALLIZATION; DERIVATIZATION; HYDROLYSIS; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 43449084642     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7026068     Document Type: Article

References (22)

1. Anderson, R. C.; Shapiro, M. J. J. Org. Chem. 1984, 49, 1304-1305.
2. 19F NMR based procedures, see: (a) Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2459.
3. (b) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519.
4. (c) Seco, J. M.; Quińoa, E.; Riguere, R. Chem. Rev. 2004, 104, 17-118.
5. For shift reagent based NMR procedures, see: (a) Whitesides, G. M.; Lewis, D. W. J. Am. Chem. Soc. 1970, 92, 6979-6980.
6. (b) Pirkle, W. H.; Beare, S. D. J. Am. Chem. Soc. 1969, 91, 5150-5155.
7. For chromatographic methods, see: (a) Schurig, V.; Nowotny, A. P. Angew. Chem., Int. Ed. Engl. 1990, 29, 939-959.
8. (b) Allenmark, S. G. Chromatographic Enantioseparation: Methods and Applications; Ellis Harwood: Chichester, U.K., 1988.
9. Quin, L. D., Verkade, J. G., Eds. Phosphorous-31 NMR Spectral Properties in Compound Characterization and Structural Analysis; VCH: Weinheim, Germany, 1994.
10. Parker, D. Chem. Rev. 1991, 91, 1441-1457.
11. Brunel, J.-M.; Pardigon, O.; Maffei, M.; Buono, G. Tetrahedron: Asymmetry 1992, 3, 1243-1246.
12. Alexakis, A.; Mutti, S.; Mangeney, P. J. Org. Chem. 1992, 57, 1224-1237.
13. Bredikhin, A. A.; Strunskaya, E. I.; Azancheev, N. M.; Bredikhina, Z. A. Russ. Chem. Bull. 1998, 47, 174-176.
14. Hulst, R.; de Vries, N. K.; Feringa, B. L. Tetrahedron: Asymmetry 1994, 5, 669-708.
15. Johnson, C. R.; Elliott, R. C.; Penning, T. D. J. Am. Chem. Soc. 1984, 104, 5019.
16. Hulst, R.; de Vries, N. K.; Feringa, B. L. Recl. Trav. Chim. Pays-Bas 1995, 114, 115-138.
17. Maki, T.; Ishihara, K.; Yamamoto, H. Org. Lett. 2005, 7, 5047-5050.
18. Lautens, M.; Tayama, E.; Herse, C. J. Am. Chem. Soc. 2005, 127, 72-73.
19. Furuta, K.; Gao, Q.; Yamamoto, H. Organic Syntheses; Wiley & Sons: New York, 1998; Collect Vol. IX, p 722.
20. Egli, M.; Dobler, M. Helv. Chim. Acta 1989, 72, 1136-1150.
21. Kadyrov, R.; Heller, D.; Selke, R. Tetrahedron: Asymmetry 1998, 9, 329-340.
22. Hartung, J.; Kneuer, R.; Rummey, C.; Bringmann, G. J. Am. Chem. Soc. 2004, 126, 12121-12129.