Determination of the absolute configuration of chiral aryl-alkyl carbinols using organophosphorus diamine derivatizing agents by 31P NMR spectroscopy

Tetrahedron Asymmetry

Volumn 15, Issue 12, 2004, Pages 1857-1879

  Chauvin, Anne Sophie ^a,b   Bernardinelli, Gérald ^a   Alexakis, Alexandre ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

^b EPFL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL ALCOHOL; DIAMIDINE DERIVATIVE; DIAMINE; METHANOL DERIVATIVE; ORGANOPHOSPHORUS COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CRYSTALLOGRAPHY; DERIVATIZATION; DIASTEREOISOMER; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PREDICTION; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

EID: 2942674673     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.04.031     Document Type: Article

References (43)

1. Wenzel T., Wilcox J.D. Chirality. 15:2003;256. and references cited therein
2. Parker D. Chem. Rev. 91:1991;1441
3. Seco J.M., Quinoa E., Riguera R. Chem. Rev. 104:2004;17
4. Latypov S.K., Ferreiro M.J., Quinoa E., Riguera R. J. Am. Chem. Soc. 120:1998;4741
5. Latypov S.K., Seco J.M., Quinoa E., Riguera R. J. Org. Chem. 61:1996;8569
6. Latypov S.K., Galiullina N.F., Aganov A.V., Kataev V.E., Riguera R. Tetrahedron. 57:2001;2231
7. Ferreiro M.J., Latypov S.K., Quinoa E., Riguera R. Tetrahedron: Asymmetry. 7:1996;2195
8. Harada N., Watanabe M., Kuwahara S., Sugio A., Kasai Y., Ichikawa A. Tetrahedron: Asymmetry. 11:2000;2843
9. Takahashi Tamiko, Fukuishima Aki, Tanaka Yuki, Takeuchi Yoshio, Kabuto Kuninobu, Kabuto Chizuko Chem. Commun. 9:2000;787
10. Yamase Hiroshi, Ooi Takashi, Kusumi Takenori Tetrahedron Lett. 39:1998;8113
11. Seco J.M., Quinoa E., Riguera R. Tetrahedron: Asymmetry. 12:2001;2915
12. Kelly D.R. Tetrahedron: Asymmetry. 101:1999;2927
13. Verkade J.-G., Quin L.-D. Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis: Organic Compounds and Metal-Complexes. Vol. 8:1987;VCH, Deerfield Beach, FL
14. Feringa B.L., Smaaardijk A., Wynberg H. Tetrahedron Lett. 27:1986;997
15. Brunel J.-M., Pardigon O., Maffrei M., Buono G. Tetrahedron: Asymmetry. 3:1992;1243
16. Anderson R.C., Shapiro M.J. J. Org. Chem. 49:1984;1304
17. Jonhson C.R., Elliott R.C., Penning T.D. J. Am. Chem. Soc. 106:1984;5019
18. Feringa B.L., Smaardijk A., Wynberg H. J. Am. Chem. Soc. 107:1985;4798
19. Feringa B.L., Smaardijk A., Wynberg H. Tetrahedron Lett. 27:1986;997
20. Feringa B.L. J. Chem. Soc., Chem. Commun. 695:1987
21. Kato N. J. Am. Chem. Soc. 112:1990;254
22. Alexakis A., Mutti S., Normant J.F., Mangeney P. Tetrahedron: Asymmetry. 1:1990;437
23. Welch J.C. Tetrahedron: Asymmetry. 2:1991;1127
24. Alexakis A., Mutti S., Mangeney P. J. Org. Chem. 57:1992;1224
25. Alexakis A., Frutos J.C., Mutti S., Mangeney P. Tetrahedron Lett. 35:1994;5125
26. Oshikawa T., Yamashita M., Kumugai S., Seo K., Kobayashi J. J. Chem. Soc., Chem. Commun. 435:1995
27. Brunel J.M., Faure B. Tetrahedron: Asymmetry. 6:1995;2353
28. Garner C.M., McWhorter C., Goerke A.R. Tetrahedron Lett. 38:1997;7717
29. de Parrodi C.A., Moreno G.E., Quintero L., Juaristi E. Tetrahedron: Asymmetry. 9:1998;2093
30. Alexakis A., Frutos J.C., Mutti S., Mangeney P. J. Org. Chem. 59:1994;3326
31. Devitt P.G., Mitchell M.C., Weetman J.M., Taylor R.J., Kee T.P. Tetrahedron: Asymmetry. 6:1995;2039
32. Reymond S., Brunel J.M., Buono G. Tetrahedron: Asymmetry. 11:2000;1273
33. Feringa B.L., Strijveen B., Kellogg R.M. J. Org. Chem. 51:1986;5484
34. Kolodiazhnyi O.I., Demchuk O.M., Gerschkovich A.A. Tetrahedron: Asymmetry. 10:1999;1729
35. Strijveen B., Feringa B.L., Kellogg R.M. Tetrahedron. 43:1987;123
36. Hulst R., de Vries N.K., Feringa B.L. Angew. Chem., Int. Ed. Engl. 31:1992;1093
37. Hulst R., Zijlstra R.W.J., de Vries N.K., Feringa B.L. Tetrahedron: Asymmetry. 9:1994;1701
38. Altomare A., Burla M.C., Camalli M., Cascarano G., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G., Spagna R. J. Appl. Cryst. 32:1999;115-119
39. Hall, S. R.; Flack, H. D.; Stewart, J. M. Eds XTAL3.2 User's Manual; Universities of Western Australia and Maryland, 1992
40. Johnson C.K. ORTEP II; Report ORNL-5138. 1976;Oak Ridge National Laboratory, Oak Ridge, TN
41. Flack H.D., Bernardinelli G. Acta Crystallogr. A55:1999;908
42. Flack H.D., Bernardinelli G. J. Appl. Crystallogr. 33:2000;1143-1148
43. Alexakis A., Chauvin A.-S., Stouvenel R., Vrancken E., Mutti S., Mangeney P. Tetrahedron: Asymmetry. 12:2001;1171