Diels-Alder reaction of 4-bromo-6-spiroepoxycyclohexa-2,4-dienone with electron-rich and neutral dienophiles

Tetrahedron

Volumn 55, Issue 2, 1999, Pages 433-448

  Bonnarme, Vincent ^a   Bachmann, Christian ^a   Cousson, Alain ^b   Mondon, Martine ^a   Gesson, Jean Pierre ^a  

^a UNIVERSITÉ DE POITIERS   (France)

^b CEA SACLAY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

4 BROMO 6 SPIROEPOXYCYCLOHEXA 2,4 DIENONE; ALKADIENE; STYRENE DERIVATIVE; UNCLASSIFIED DRUG; VINYL ACETATE;

ARTICLE; CATALYSIS; CYCLIZATION; DIASTEREOISOMER; OXIDATION; PHASE TRANSITION; PRIORITY JOURNAL; REACTION ANALYSIS;

BETULACEAE;

EID: 0033534434     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01041-2     Document Type: Article

References (47)

1. (a) Adler, E.; Brasen, S.; Miyake, H. Acta Chem. Scand. 1971, 25, 2055.
2. (b) Becker, H.-D.; Bremholt, T.; Adler, E. Tetrahedron Lett. 1972, 4205.
3. (a) Adler, E.; Holmberg, K. Acta Chem. Scand. 1974, B 28, 465.
4. (b) Cacioli, P.; Reiss, J.A. Aust. J. Chem. 1984, 37, 2525.
5. (a) Corey, E.J.; Dittami, J.P. J. Am. Chem. Soc. 1985, 107, 256.
6. (b) Yamashita, D.S.; Rocco, V.P.; Danishefsky, S.J. Tetrahedron Lett. 1991, 32, 6667.
7. (c) Haseltine, J.N.; Cabal, M.P.; Mantlo, N.B.; Iwasara, N., Yamashita, D.S.; Coleman, R.S.; Danishefsky, S.J.; Schulte, G.K. J. Am. Chem. Soc. 1991, 113, 3850.
8. (a) Singh, V.; Thomas, B. J. Chem. Soc. Chem. Commun. 1992, 1211.
9. (b) Singh, V.; Porinchu, M. J. Chem. Soc. Chem. Commun. 1993, 134.
10. (c) Gesson, J.-P.; Hervaud, L. Mondon, M. Tetrahedron Lett. 1993, 34, 2941.
11. (d) Singh, V., Porinchu, M. Tetrahedron 1996, 52, 7087.
12. Becker, H.-D.; Ruge, B. J. Org. Chem. 1980, 45, 2189.
13. Metlesics, W.; Wessely, F.; Budzikiewicz, H. Monatsch. Chemie 1958, 89, 102 and references cited therein.
14. (a) Auksi, H.; Yates, P. Can. J. Chem. 1981, 59, 2510.
15. (b) Sing, V.; Sharma, U.; Prasanna, V.; Porinchu, M. Tetrahedron, 1995, 51, 6015 and references cited therein.
16. (a) Bhamare, N.K.; Granger, T.; Macas, T.S.; Yates, P. J. Chem. Soc. Chem. Commun. 1990, 739.
17. (b) Singh, V.; Alam, S.Q.; Porinchu, M. Tetrahedron 1995, 51, 13423.
18. (c) Singh, V; Deota, P.T., Bedekar, A.V. J. Chem. Soc. Perkin Trans I 1992, 903.
19. Singh, V.; Thomas, B. J. Org. Chem. 1997, 62, 5320.
20. Jones, D. W. J. Chem. Soc (C), 1969,1729.
21. Harano, K.; Aoki, T., Ho, M.; Hisano, T. Chem. Pharm. Bull. 1990, 38, 1182.
22. Afarinkia, K.; Daly, N. T.; Gomez-Famos, S.; Joshi, S. Tetrahedron Lett. 1997, 38, 2369.
23. (a) Dewar, M. J. S.; Zoebish, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
24. (b) Liotard, D. A.; Healy, E. F.; Ruiz, J. M.; Dewar, M. J. S., QCPE 506 1989.
25. 14b In each case, the fully optimized TS's were characterized by one and only one imaginary frequency corresponding to the concerted cycloaddition. No account has been made of zero point energy corrections. Though these corrections are not negligible in barrier height calculations, they probably become negligible in selectivity studies where similar reactions are compared.
26. (b) Powell, M. J. D., Numerical Methods for Nonlinear Algebraic Equations, Rabinowitz, Ed., Gordon and Breach, New York, 1970, Chaps 6 & 7.
27. The percentage of adducts have been evaluated assuming that the product distribution is under kinetic control and the relative percentages were then calculated in the context of the transition state theory at 300°K.
28. Dewar, M. J. S.; Olivella, S.; Stewart, J. J. P. J. Am. Chem. Soc. 1986, 108, 5771.
29. Werstiuk, N. H.; Ma, J. Can. J. Chem. 1994, 72, 2493.
30. Sisti, N. J.; Motorina, I. A.; Tran Huu Dau, M.-E.; Riche, C.; Fowler, F. W.; Grierson, D. S. J. Org. Chem. 1996, 61, 3715.
31. Fleming, I. Frontier Orbitals and Organic Chemical Reactions, Wiley: New York, 1976.
32. Additional AM1 calculations reveal interesting trends concerning the LUMO of 1. Indeed, the C5 coefficient (0.49) is significantly larger than the C2 coefficient (0.42). Substituting the 4-bromo substituent by a hydrogen leads to similar C5 and C2 coefficients (0.45 and 0.43 respectively). Retaining the bromo substituent and substituting the carbonyl group by a methylene again leads to significantly different C5 and C2 coefficients (0.58 and 0.49 respectively). From these AM1 results, it appears that the 4-bromo substituent generates a larger LUMO CS coefficient and thus, this bromo effect may lead to an enhanced regioselectivity.
33. Sauer, J.; Sustmann, R. Angew. Chem. Int. Ed. Engl. 1980, 19, 779.
34. (a) Pyckhout, W.; Van Nuffel, P.; Van Alsenoy, C.; Van Den Enden, L.; Geise, H.J. J. Mol. Struct. 1983, 102, 333.
35. (b) Sullivan, J.F.; Dickson, T.J.; Durig, J.R. Spectrochim. Acta 1986, 42A, 113.
36. Ruiz-Lopez, M F.; Assfeld, X.; Garcia, J. I.; Mayoral, J. A.; Salvatella, L. J. Am. Chem. Soc. 1993, 115, 8780.
37. Liu, J.; Niwayama, S.; You, Y.; Houk, K.N. J. Org. Chem. 1998, 63, 1064.
38. 24b an hypothetical s-cis,s-trans structure is shown to rearrange to the s-trans,s-trans conformer.
39. (b) Gaussian 94 (Revision B.2), Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B., Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L., Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A., Gaussian, Inc., Pittsburgh, PA, 1995.
40. For instance, the s-cis methyl formate is more stable than the s-trans conformer by about 5-6 kcal/mol. For a discussion on this point, including experimental data and ab initio calculations, see Eliel, E.L.; Wilen, S.H. Stereochemistry of Organic Compounds; Wiley: New-York, 1994.
41. Goldstein, E.; Beno, B.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 6036.
42. (a) Macaulay, J.B.; Fallis, A. J. Am. Chem. Soc. 1990, 112, 1136 and references cited therein.
43. (b) Froese, R.D.J.; Organ, M.G.; Goddard, J.D.; Stack, T.D.P.; Trost, B.M. J. Am. Chem. Soc. 1995, 117, 10931.
44. Paquette, L. A.; Branan, B. M.; Rogers, R. D.; Bond, A. H.; Lange, H., Gleiter, R, J. Am. Chem. Soc. 1995, 117, 5992 and references cited therein.
45. Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 663.
46. Sheldrick, G.M. SHELXS86, Program for the Solution of Crystal Structures, 1986, University of Göttingen, Germany.
47. Watkin, D.J.; Carruthers, J.R.; Betteridge, P.W. CRYSTALS Software, 1985, Chemical Crystallography Laboratory, University of Oxford.