General method of assignment of relative stereochemistry in C-1-substituted 2,4-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one by 1H and 13C NMR correlations

Magnetic Resonance in Chemistry

Volumn 36, Issue 3, 1998, Pages 174-180

  Montaña, Angel M ^a   Ribes, Sandra ^a   Grima, Pedro M ^a   García, Francisca ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

8 oxabicyclo 3.2.1 oct 6 en 3 one; 13C NMR; 1H NMR; Assignment of relative stereochemistry; NMR; Spectral data correlation

Indexed keywords

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOSELECTIVITY;

13C NMR; 1H NMR; 8-OXABICYCLO-[3.2.1]-OCT-6-EN-3-ONE; ASSIGNMENT OF RELATIVE STEREOCHEMISTRY; DATA CORRELATIONS; DIASTEREOISOMERS; GENERAL METHOD; NMR SPECTRUM; SPECTRAL DATA; SPECTRAL DATA CORRELATION;

CHEMICAL SHIFT;

EID: 0032331181     PISSN: 07491581     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1097-458x(199803)36:3<174::aid-omr242>3.3.co;2-p     Document Type: Article

References (40)

1. (a) H. M. R. Hoffmann, Angew. Chem., Int. Ed. Engl. 23, 1 (1984);
2. (b) J. Mann, Tetrahedron, 42, 4611 (1986).
3. (a) A. M. Montana and K. M. Nicholas, Magn. Reson. Chem. 28, 486 (1990);
4. (b) J. W. Blunt, A. Burrit, J. M. Coxon and P. J. Steel, Magn. Reson. Chem. 34, 131 (1996);
5. (c) T. Ishizu, M. Mori and K. Kanematsu, J. Org. Chem. 46, 526 (1981);
6. (d) H. M. R. Hoffmann, K. E. Clemens and R. H. Smithers, J. Am. Chem. Soc. 94, 3940 (1972);
7. (e) J. G. Vinter and H. M. R. Hoffmann, J. Am. Chem. Soc. 96, 5466 (1974);
8. (f) H. M. L. Davies, N. J. S. Huby, W. R. Cantrell and J. L. Olive, J. Am Chem. Soc. 115, 9468 (1993);
9. (g) D. I. Rawson, B. K. Carpenter and H. M. R. Hoffmann. J. Am Chem. Soc. 101, 1786 (1979).
10. M. R. Ashcroft and H. M. R. Hoffmann, Org. Synth. 58, 17 (1978).
11. A. Hosomi and Y. Tominaga, In Comprehensive Organic Chemistry, edited by B. Trost and I. Fleming, pp. 593-615. Pergamon Press, Vol. 5, Oxford (1995).
12. (a) L. M. Jackman and S. Sternhell, Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, pp. 52 and 104. Pergamon Press, New York, (1969);
13. (b) P. Laszlo, Prog. Nucl. Magn. Reson. Spectrosc. 3, 231 (1967).
14. (a) D. Neuhans and M. Williamson, The Nuclear Overhauser Effect in Structural and Conformational Analysis, pp 211, 253, 353 and 421. VCH, New York, (1989);
15. (b) J. H. Noggle and R. E. Schirmer, The Nuclear Overhauser Effect: Chemical Applications. Academic Press, New York (1972);
16. (c) H. M. L. Davies, N. J. S. Huby, W. R. Cantell and J. L. Olive, J. Am. Chem. Soc. 115, 9470 (1993).
17. (a) H. M. R. Hoffmann, K. E. Clemens, and R. H. Smithers, J. Am. Chem. Soc. 94, 3940 (1972);
18. (b) B. Waegell and G. Ourisson, Bull. Soc. Chim. Fr. 495, 496, 503 (1963);
19. (b) B. Waegell and C. W. Jefford, Bull. Soc. Chim. Fr. 844 (1964);
20. (d) C. W. Jefford, A. Baretta, J. Fournier and B. Waegell, Helv. Chim. Acta 53, 1180 (1970);
21. (e) C. W. Jefford and U. Burger, Chimia 24, 385 (1970).
22. (a) M. P. Schweizer, S. I. Chan, G. K. Helmkamp and P. O. P. Tso, J. Am. Chem. Soc. 86, 696 (1964);
23. (b) H. M. R. Hoffmann, Angew. Chem., Int. Ed. Engl. 12, 819 (1973);
24. (c) L. M. Jackman and S. Sternhell, Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, p. 67. Pergamon Press, Oxford (1969).
25. L. M. Jackman and S. Sternhell, Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, p. 88. Pergamon Press, Oxford (1969).
26. H. M. L. Davies, N. S. Huby, W. R. Cantrell and J. L. Olive, J. Am. Chem. Soc. 115, 9470 (1993).
27. F. W. Wehrli and T. Wirthling, Interpretation of Carbon 13 NMR Spectra, p. 37. Wiley, New York (1976).
28. A. M. Montaña, S. Ribes, P. M. Grima and F. García, Tetrahedron 53, 11669 (1997).
29. H. Kessler, M. Gehrke and C. Griesinger, Angew. Chem., Int. Ed. Engl. 27, 490 (1988).
30. D. M. Doddrell, D. T. Pegg and M. R. Bendall, J. Magn. Reson. 48, 323 (1982).
31. (a) W. P. Ane, E. Bartholdi and R. R. Ernst, J. Chem Phys. 64, 2229 (1976);
32. (b) K. Nagayama, A. Kumar, K. Wüthrich and R. R. Ernst, J. Magn. Reson. 40, 321 (1980).
33. (a) G. Bodenhausen, H. Kogler and R. R. Ernst, J. Magn. Reson. 58, 370 (1984);
34. (b) G. Wider, S. Macura, A. Kumar, R. R. Ernst and K. Wüthrich, J. Magn. Reson. 56, 207 (1984);
35. (c) J. Jeen, B. H. Meier, P. Backmann and R. R. Ernst, J. Chem. Phys. 71, 4546 (1979);
36. (d) A Kumar, R. R. Ernst and K. Wüthrich, Biochem. Biophys. Res. Commun. 95, 1 (1980).
37. G. E. Martin and A. S. Zektzer, Two-Dimensional NMR Methods for Establishing Molecular Connectivity, p. 171. VCH, New York, (1988).
38. A. Bax and S. Subramanian, J. Magn. Reson. 61, 565 (1986).
39. J. R. Carbow, D. P. Weitekamp and A. Pines, Chem. Phys. Lett. 93, 504 (1982).
40. A. Bax and M. F. Summers, J. Am. Chem. Soc. 108, 2093 (1986).