Identification of chiral cis- and trans-2-stannyloxazolidines by their NMR spectra and solid-state structures

European Journal of Organic Chemistry

Volumn , Issue 20, 2004, Pages 4268-4279

  Cintrat, Jean Christophe ^a   Léat Crest, Véronique ^a   Parrain, Jean Luc ^a   Le Grognec, Erwan ^a   Beaudet, Isabelle ^a   Toupet, Loïc ^b   Quintard, Jean Paul ^a  

^a Centre National de la Recherche Scientifique   (France)

^b CNRS   (France)

Author keywords

Configuration determination; Conformation; NMR spectroscopy; Oxazolidine; Tin

Indexed keywords

2 STANNYLOXAZOLIDINE; 2 TRIBUTYLSTANNYL 1,3 OXAZOLIDINE; 2 TRIMETHYLSTANNYL 1,3 OXAZOLIDINE; 2 TRIPHENYLSTANNYL 1,3 OXAZOLIDINE; 3 (TERT BUTOXYCARBONYL) 4 ISOPROPYL 2 TRIPHENYLSTANNYL 1,3 OXAZOLIDINE; 3 (TERT BUTOXYCARBONYL) 4 PHENYL 2 TRIMETHYLSTANNYL 1,3 OXAZOLIDINE; 3 (TERT BUTOXYCARBONYL) 4 PHENYL 2 TRIPHENYLSTANNYL 1,3 OXAZOLIDINE; 3 ALKOXY 2 TRIBUTYLSTANNYL 1,3 OXAZOLIDINE; 3 ALKOXYCARBONYL 2 TRIBUTYLSTANNYL 1,3 OXAZOLIDINE; 3 SULFONYL 2 TRIBUTYLSTANNYL 1,2 OXAZOLIDINE; OXAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CRYSTAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; X RAY CRYSTALLOGRAPHY;

EID: 8444226450     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400203     Document Type: Article

References (46)

1. J.-C. Cintrat, V. Léat-Crest, J.-L. Parrain, E. Le Grognec, I. Beaudet, J.-P. Quintard, Eur. J. Org. Chem. 2004, 4263-4279, preceding article.
2. L. Colombo, M. Di Giacomo, G. Brusotti, G. Delogu, Tetrahedron Lett. 1994, 35, 2063-2066.
3. L. Colombo, M. Di Giacomo, G. Brusotti, E. Milano, Tetrahedron Lett. 1995, 36, 2863-2866.
4. L. Colombo, M. Di Giacomo, Tetrahedron Lett. 1999, 40, 1977-1980.
5. J. C. Cintrat, V. Léat, J.-L. Parrain, E. Le Grognec, I. Beaudet, L. Toupet, J.-P. Quintard, Organometallics 2004, 23, 943-945.
6. D. Seebach, B. Lamatsch, R. Amstutz, A. K. Beck, M. Dobler, M. Egli, R. Fitzi, M. Gautschi, B. Herradon, P. C. Hidber, J. J. Irwin, R. Locher, M. Maestro, T. Maetzke, A. Mouriño, E. Pfammatter, D. A. Plattner, C. Schickli, W. B. Schweizer, P. Seiler, G. Stucky, W. Petter, J. Escalante, E. Juaristi, D. Quintana, C. Miravitlles, E. Molins, Helv. Chim. Acta 1992, 75, 913-934.
7. J. C. Martins, M. Biesemans, R. Willem, Prog. NMR Spectrosc. 2000, 36, 271-322 and references herein.
8. B. Wrackmeyer, Annu. Rep. NMR Spectrosc. 1999, 38, 203-264.
9. M. Karplus. J. Chem. Phys. 1959, 30, 11-15.
10. L. Belvisi, O. Carugo, G. Poli, J. Mol. Struct. 1994, 318, 189-202.
11. M. Santagio, E. Low, G. Chambournier, R. E. Gawley, J. Org. Chem. 2003, 68, 8480-8484.
12. D. Doddrell, I. Burfitt, W. Kitching, M. Bullpitt, C. H. Lee, R. J. Mynott, J. L. Considine, H. G. Kuivila, R. H. Sarma, J. Am. Chem. Soc. 1974, 96, 1640-1642.
13. W. Kitching, Org. Magn. Reson. 1982, 20, 123-124.
14. T. N. Mitchell, J. C. Podesta, A. Ayala, A. B. Chopa, Magn. Reson. Chem. 1988, 26, 497-500.
15. J.-P. Quintard, M. Degueil-Castaing, B. Barbe, M. Pétraud, J. Organomet. Chem. 1982, 234, 41-61.
16. T. N. Mitchell, H. J. Belt, J. Organomet. Chem. 1990, 386, 167-176.
17. T. N. Mitchell, W. Reimann, C. Nettelbeck, Organometallics 1985, 4, 1044-1048.
18. J.-F. Betzer, P. Le Menez, J. Prunet, J.-D. Brion, J. Ardisson, A. Pancrazi, Synlett 2002, 1-15.
19. R. Carleer, M. J. O. Anteunis, Org. Magn. Res. 1979, 12, 673-678.
20. J.-P. Quintard, G. Dumartin, C. Guérin, J. Dubac, A. Laporterie, J. Organomet. Chem. 1984, 266, 123-138.
21. E. L. Eliel, S. H. Wilen, L. N. Mander, in Stereochemistry of Organic Compounds, John Wiley & Sons, New York, 1994.
22. A. Duchêne, S. Boissière, J.-L. Parrain, J.-P. Quintard, J Organomet. Chem. 1990, 387, 153-162.
23. G. M. Drew, W. Kitching, J. Org. Chem. 1981, 46, 558-570.
24. G. Dumartin, J.-P. Quintard, M. Pereyre, J. Organomet. Chem. 1980, 185, C34-C36.
25. G. Wickham, D. Young, W. Kitching, J. Org. Chem. 1982, 47, 4884-4895.
26. J.-P. Quintard, M. Degueil-Castaing, G. Dumartin, B. Barbe, M. Pétraud, J. Organomet. Chem. 1982, 234, 27-40.
27. A. Rahm, J. Grimeau, M. Pétraud, B. Barbe, J. Organomet. Chem. 1985, 286, 297-304.
28. U. Salzner, J. Org. Chem. 1995, 60, 986-995.
29. H. Günther, La spectroscopie de RMN (French translation, J.-J. Suffert, J. Suffert) 1994, Masson, Paris, pp. 112-136.
30. M. Pereyre, J.-P. Quintard, A. Rahm, Pure Appl. Chem. 1982, 54, 29-41.
31. P. J. Smith, A. P. Tupciauskas, Ann. Rep. NMR Spectrosc. 1978, 8, 291-370.
32. J.-C. Cintrat, Ph.D. Thesis, University of Nantes 1995.
33. J.-L. Parrain, I. Beaudet, J.-C. Cintrat, A. Duchêne, J.-P. Quintard, Bull. Soc. Chim. Fr. 1994, 131, 304-312.
34. J.-P. Quintard, B. Elissondo, D. Mouko-Mpegna, J. Organomet. Chem. 1983, 257, 175-187.
35. D. T. Cromer, J. T. Waber, in International Tables for X-ray Crystallography, vol. IV, The Kyroch Press, Birmingham, England, 1974.
36. G. M. Sheldrick, Crystallographic Computing 3: Data Collection, Structure determination, Proteins and Databases (Eds.: G M. Sheldrick, C. Krüger, R. Goddard), Clarendron Press, Oxford, England, 1985.
37. C. K. Fair, MOLEN, An intelligent system for Crystal Structure Analysis, Enraf - Nonius, Delft, The Netherlands.
38. M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid Plot Program for Crystal Structure Illustrations, Oak Ridge National Laboratory Report ORNL-6895, 1996.
39. Nonius KappaCCD Software, Nonius BV, Delft, The Netherlands, 1999, pp. 307-326.
40. Z. Otwinowski, W. Minor, Processing of X-ray Diffraction Data Collected in Oscillation Mode, in Methods in Enzymology, vol. 276, Macromolecular Crystallography Part A (Eds.: C. W. Carter, R. M. Sweet).
41. A. Altomare, M. C. Burla, M. Camalli, M. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G Moliterni, G Polidori, R. Spagna, J. Appl. Cryst. 1998, 31, 74-77.
42. G. M. Sheldrick, SHELX97, Program for the refinement of Crystal Structures, 1997, University of Göttingen, Germany.
43. International tables for X-ray crystallography, (Ed.: A. J. C.), Kluwer Academic Publishers, Dordrecht, The Netherlands, 1992, vol. C.
44. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Jr. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian 98; Gaussian, Inc.: Pittsburgh, PA, 1998.
45. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
46. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.