Planar chiral cyclic ether: Asymmetric resolution and chirality transformation

Journal of the American Chemical Society

Volumn 127, Issue 35, 2005, Pages 12182-12183

  Tomooka, Katsuhiko ^a   Komine, Nobuyuki ^a   Fujiki, Daisuke ^a   Nakai, Takeshi ^a   Yanagitsuru, Syun Ichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKENE; ETHER DERIVATIVE; HETEROCYCLIC COMPOUND; OXAZOLINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CRYSTAL STRUCTURE; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KINETICS; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 24644451948     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja053347g     Document Type: Article

References (39)

1. Blomquist, A. T.; Liu, L. H.; Bohrer, J. C. J. Am. Chem. Soc. 1952, 74, 3643-3647.
2. For reviews, see: (a) Marshall, J. A. Acc. Chem. Res. 1980, 13, 213-218.
3. (b) Nakazaki, M.; Yamamoto, K.; Naemura, K. Top. Curr. Chem. 1984, 125, 1-25.
4. (c) Schlögl, K. Top. Curr. Chem. 1984, 125, 27-62.
5. (d) Eliel, E. L.; Wilen, S. H.; Mander, L. N. In Stereochemistry of Organic Compounds: Wiley: New York, 1994; pp 1172-1175.
6. For representative studies on planar chiral cycloalkenes, see: (a) Cope, A. C.; Howell, C. F.; Knowles, A. J. Am. Chem. Soc. 1962, 84, 3190-3191.
7. (b) Cope, A. C.; Ganellin, C. R.; Johnson, H. W., Jr. J. Am. Chem. Soc. 1962, 84, 3191-3192.
8. (c) Cope, A. C.; Mehta, A. S. J. Am. Chem. Soc. 1964, 86, 5626-5630.
9. (d) Cope, A. C.; Banholzer, K.; Keller, H.; Pawson, B. A.; Whang, J. J.; Winkler, H. J. S. J. Am. Chem. Soc. 1965, 87, 3644-3649.
10. (e) Cope, A. C.; Pawson, B. A. J. Am. Chem. Soc. 1965. 87, 3649-3651.
11. (f) Binsch, G.; Roberts, J. D. J. Am. Chem. Soc. 1965, 87, 5157-5162.
12. (g) Manor, P. C.; Shoemaker, D. P.; Parkes, A. S. J. Am. Chem. Soc. 1970, 92, 5260-5262.
13. (h) Marshall, J. A.; Konicek, T. R.; Flynn, K. E. J. Am. Chem. Soc. 1980, 102, 3287-3288.
14. (i) Inoue, Y.; Matsushima, E.; Wada, T. J. Am. Chem. Soc. 1998, 120, 10687-10696.
15. (j) Hoffmann, R.; Inoue, Y. J. Am. Chem. Soc. 1999, 121, 10702-10710 and references cited therein.
16. Recently, chiral silacycloheptene has been synthesized: (k) Krebs, A.; Pforr, K.-I.; Raffay, W.; Thölke, B.; König, W. A.; Hardt, I.; Boese, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 159-160.
17. (l) Krebs, A.; Thölke, B.; Pforr, K.-I.; König, W. A.; Scharwächter, K.; Grimme, S.; Vögtle, F.; Sobanski, A.; Schramm, J.; Hormes, J. Tetrahedron: Asymmetry, 1999, 10, 3483-3492.
18. For reactions involving planar chiral cyclic intermediate, see: (m) Wharton, P. S.; Johnson, D. W. J. Org. Chem. 1973, 38, 4117-4121.
19. (n) Gauvreau, D.; Barriault, L. J. Org. Chem. 2005, 70, 1382-1388.
20. For recent reports on planar chirality of medium-sized ring containing central chirality. see: (a) Sudau, A.; Münch, W.; Nubbemeyer, U. J. Org. Chem. 2000, 65, 1710-1720.
21. (b) Nubbemeyer, U. Eur. J. Org. Chem. 2001, 1801-1816 and references cited therein.
22. (c) Deiters, A.; Mück-Lichtenfeld, C.; Fröhlich, R.; Hoppe, D. Chem.-Eur. J. 2002, 8, 1833-1842.
23. (a) Tomooka, K.; Komine, N.; Nakai, T. Tetrahedron Lett. 1998, 39, 5513-5516.
24. (b) Tomooka, K.; Yamamoto, K.; Nakai, T. Angew. Chem., Int. Ed. 1999, 38, 3741-3743.
25. (c) Tomooka, K.; Wang, L. F.; Okazaki, F.; Nakai, T. Tetrahedron Lett. 2000, 41, 6121-6125.
26. Marshall, J. A.; Lebreton, J. J. Org. Chem. 1988, 53, 4108-4112.
27. Ether 1a was prepared from neryl acetate in four steps by a slight modification of the procedure described by Marshall (ref 6): see the Supporting Information.
28. 1H NMR analysis of MTPA ester (for 3a, 3b, and 7).
29. 2. See: Anglea, T. A.; Pinder, A. R. Tetrahedron 1987, 43, 5537-5543.
30. It is worth noting that Marshall and Lebreton recognized the possibility of chirality of 1a, but measured no optical activity in the recovered material (10% yield) upon chiral base-promoted [2,3]-Wittig rearrangement.
31. Only a trace amount of racemization (< 1%) was detected by chiral HPLC analysis, when it was maintained at 25 °C in hexane for 2 weeks.
32. Conformational analysis of ether 1a was carried out with the MacroModel 8.0 package and PC Spartan Pro 1.0.5. Conformational search was performed with the Mixed MCMM/LowMode method (5000 structures) using the MM2* force field. Further geometry optimization and the potential energy calculation of the most stable conformers were performed by PM3 calculation using Spartan.
33. 1H NMR analyses. Significantly, no appreciable change in peak shape and width was observed up to 110 °C, while at around 80 °C, 1a began to undergo the Cope rearrangement.
34. The absolute stereochemistry of (R,R)-3b was determined by the modified Mosher's method. See: Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096.
35. The absolute stereochemistry of 4, 7, and 9 was deduced from the configuration of 1a and the steric course of the reactions.
36. The structure of 6 was determined by X-ray crystallography; see the Supporting Information. It is worth noting that the nine-membered carbon framework of the X-ray crystal structure of diepoxide 6 is found to be superimposable to the framework of the calculated conformation of ether 1a. It shows the validity of the proposed conformation of 1a.
37. Palucki, M.; McCormick, G. J.; Jacobsen, E. N. Tetrahedron Lett. 1995, 36, 5457-5460.
38. Brown, H. C.; Desai, M. C.; Jadhav, P. K. J. Org. Chem. 1982, 47, 5065-5069.
39. Overman, L. E.; Renaldo, A. F. Tetrahedron Lett. 1983, 24, 3757-3760.