Dienophilic behavior of (S)-2-p-tolylsulfinyl butenolide

Tetrahedron

Volumn 53, Issue 41, 1997, Pages 14115-14126

  Carretero, Juan Carlos ^a   García Ruano, Jose Luis ^a   Martín Cabrejas, Luisa M ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

NORBORNANE DERIVATIVE; POLYCYCLIC HYDROCARBON;

ARTICLE; CHIRALITY; DRUG PURIFICATION; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030777259     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00913-7     Document Type: Article

References (28)

1. a) de Jong, J. C.; van Bolhuis, F.; Feringa, B. L. Tetrahedron: Asymmetry, 1991, 2, 1247 (and references cited therein).
2. b) Casas, R.; Parella, T.; Branchadell, V.; Oliva, A.; Ortuño, R. M.; Guingant, A. Tetrahedron 1992, 48, 2659 (and references cired therein).
3. c) Branchadell, V.; Sodupe, M.; Ortuño, R. M.; Oliva, A.; Gómez-Pardo, D.; Guingant, A.; d'Angelo, J. J. Org. Chem. 1991, 56, 4135.
4. See Arai, Y.; Koizumi, T. Sulfur Reports 1993, Vol. 15, pp 41-65 and references cited therein.
5. Carretero, J. C.; García Ruano, J. L.; Lorente, A.; Yuste, F. Tetrahedron: Asymmetry 1993, 4, 177. For the Diels Alder reactions of enantiomerically pure sulfinyl maleimides, see: Arai, Y.; Matsui, M.; Koizumi, T.; Shiro, M. J. Org. Chem. 1991, 56, 1983.
6. Carretero, J. C.; García Ruano, J. L.; Lorente, A.; Yuste, F. Tetrahedron: Asymmetry 1993, 4, 177. For the Diels Alder reactions of enantiomerically pure sulfinyl maleimides, see: Arai, Y.; Matsui, M.; Koizumi, T.; Shiro, M. J. Org. Chem. 1991, 56, 1983.
7. Alonso, I.; Carretero, J. C.; García Ruano, J. L. Tetrahedron Lett. 1989, 30, 3853.
8. Alonso, I.; Carretero J. C. ; García Ruano, J. L.; Martin Cabrejas, L. M.; López Solera, I.; Raithby, P. R. Tetrahedron Lett. 1994, 35, 9461.
9. For the use of 2 and 3 as Michael acceptors, see: Posner, G. H. Acc. Chem. Res. 1987, 20, 72.
10. Posner, G. H.; Frye, L. L.; Hulce, M. Tetrahedron 1984, 40, 1401.
11. Holton R. A.; Kim, H.-B. Tetrahedron Lett. 1986, 27, 2191.
12. Hamdouchi, C.; Ph. D. Thesis, E.H.I.C.S., Estrasbourg, 1991.
13. The use of bases or solvents different to those indicated (NaOH and i-PrOH) determines a substantial decrease of the yields.
14. If the hydroxyacid intermediate is isolated, as described in ref. 7, the yield in the preparation of 2 is much lower (46% from 4).
15. Significant NOE's of endo-6A and endo-6B. (matrix presented)
16. Jones, G.; Raphael, R. A.; Wright, S. J. Chem. Soc. Perkin Trans. 1, 1974, 1676.
17. a) Carretero, J. C.; García Ruano, J. L.; Martín Cabrejas, L. M. Tetrahedron: Asymmetry 1997, 8, 0000.
18. b) Arai, Y.; Kuwayama, S.-I.; Takeuchi, Y.; Koizumi, T. Tetrahedron Lett. 1985, 26, 6205. See also:
19. c) Arai, Y.; Takayama, H.; Koizumi, T. Tetrahedron Lett. 1987, 28, 3689.
20. 0 donor-acceptor interaction, as well as a higher (less likely) electrostatic repulsion between the oxygens in these rotamers could be invoked to explain the larger population of the rotamers like B in acyclic esters and consequently the higher π-facial selectivity of their cycloadditions.
21. 0 donor-acceptor interaction, as well as a higher (less likely) electrostatic repulsion between the oxygens in these rotamers could be invoked to explain the larger population of the rotamers like B in acyclic esters and consequently the higher π-facial selectivity of their cycloadditions.
22. Carretero, J. C.; García Ruano, J. L.; Martín Cabrejas, L. M. Tetrahedron 1995, 51, 8323.
23. a) Alonso, I.; Carretero, J. C.; García Ruano, J. L. J. Org. Chem. 1993, 58, 3231.
24. b) Alonso, I.; Carretero, J. C.; García Ruano, J. L. J. Org. Chem. 1994, 59, 1499.
25. a) Junning, L.; Snyder, J. S. J. Org. Chem. 1990, 55, 4995.
26. b) Symmes, C.; Quin, L.D. J. Org. Chem. 1979, 44, 1048.
27. c) Hajos, Z. H.; Parrish, D. R.; Goldberg, M. W. J. Org. Chem. 1965, 1213.
28. d) Robins, P. A.; Walker, J. J. Chem. Soc. 1956, 3249.