Regiochemical control in asymmetric Diels-Alder cycloadditions of enantiopure (S)S-(p-Tolylsulfinyl)-1,4-benzoquinones with Dane's diene

Tetrahedron Letters

Volumn 38, Issue 52, 1997, Pages 9077-9080

  Carreño, M Carmen ^a   García Ruano, José L ^a   Remor, Cynthia Z ^a,c   Urbano, Antonio ^a   Fischer, Jean ^b  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b UNIVERSITÉ DE STRASBOURG   (France)

^c FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZOQUINONE; BENZOQUINONE DERIVATIVE;

ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; ENANTIOMER; STEREOCHEMISTRY;

BETULACEAE;

EID: 0030780303     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10439-7     Document Type: Article

References (27)

1. For an overview of our work, see: a) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760.
2. For more recent references, see: b) Carreño, M. C.; García Ruano, J. L.; Toledo, M. A.; Urbano, A.; Stefani, V.; Remor, C. Z.: Fischer, J. J. Org. Chem. 1996, 61, 503-509;
3. c) Carreño, M. C.; García Ruano, J. L.; Urbano, A.; Hoyos, M. A. J. Org. Chem. 1996, 61, 2980-2985.
4. d) Carreño, M. C.; García Ruano, J. L.; Urbano, A.; López-Solera, M. I. J. Org. Chem. 1997, 62, 976-981.
5. e) Carreño, M. C.; Mahugo, J.; Urbano, A. Tetrahedron Lett. 1997, 38, 3047-3050.
6. f) Carreño, M. C.; Urbano, A.; Fischer, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1621-1623.
7. Areniyadis, S.; Rodríguez, R.; Yashunsky, D. V.; Cámara, J.; Ourisson, G. Tetrahedron Lett. 1994, 35, 4843-4846.
8. Dane, E.; Schmitt, J. Liebigs Ann. Chem. 1938, 556, 196; ibid 1939, 537, 246.
9. Dane, E.; Schmitt, J. Liebigs Ann. Chem. 1938, 556, 196; ibid 1939, 537, 246.
10. b) Robins, D. A.; Walker, J. J. Chem. Soc. 1956, 3249.
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18. h) Alonso, I.; Carretero, J. C.; García Ruano, J. L.; Martín Cabrejas, L. M.; López-Solera, L; Raithby, R. Tetrahedron Lett. 1994, 35, 9461-9464.
19. i) Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 1996, 37, 7403-7406.
20. Carreńo, M. C; García Ruano, J. L.; Urbano, A. Synthesis 1992, 651-653.
21. Carreño, M. C.; García Ruano, J. L.; Toledo, M. A.; Urbano, A. Tetrahedron:Asymmetry 1997, 8, 913-921.
22. 1H-NMR δ 8.05 and 7.95 (AB system, 2H, J = 8.2 Hz), 7.67 (d, 1H, J = 8.6 Hz), 6.89 (dd, 1H, J = 2.7 and 8.6 Hz), 6.80 (d, 1H, J = 2.7 Hz), 6.78 (q, 1H, J = 1.6 Hz), 3.87 (s, 3H), 3.50 and 2.81 (2dd, 4H, J = 7.0 and 7.5 Hz), 2.19 (d, 3H, J= 1,6 Hz).
23. 1H-NMR analysis using Yb(hfc)3 as chiral lantanide shift reagent. Racemic compounds necessary for such evaluation were obtained starting from racemic quinones (±)-2 and (±)-3.
24. The structures of (+)-6 and (-)-8 were assigned from HMBC and HMQC spectral data and the regiochemistry of aromatic compound 7, which resulted from (+)-6, was confirmed by X-ray difraction.
25. 2 and/or lower temperatures, the ratio between (+)-6 and (-)-8 changed in favour of 6, showing a decreasing association between the Lewis acid and the basic centre of diene 1.
26. In the case of compound 4, a change in both regiochemistry and it-facial diastereoselectivity from thermal to Lewis acid conditions would give the same enantiomer.
27. Fleming, I. Frontier Orbitals and Organic Chemical Reactions : John Wiley & Sons New York, 1976.