Intramolecular Diels-Alder reactions with substituted Feringa-butenolides: a dramatic increase in reactivity by double activation

Tetrahedron Asymmetry

Volumn 11, Issue 16, 2000, Pages 3345-3349

  Reiser, Ulrich ^a   Jauch, Johann ^a   Herdtweck, Eberhardt ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BUTENOLIDE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; TEMPERATURE; X RAY ANALYSIS;

EID: 0034714175     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00286-X     Document Type: Article

References (25)

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11. 2 with SHELXL-97 weighting scheme and stopped at shift/err <0.001. The correct enantiomer is fixed by the synthetic route and confirmed by Flack's parameter x=0.10 (9). Neutral atom scattering factors for all atoms and anomalous dispersion corrections for the non-hydrogen atoms were taken from International Tables for Crystallography. All calculations were performed on a DEC 3000 AXP workstation and an Intel Pentium II PC, with the Strux-V system, including the programs Platon, Sir92, and SHELXL-97.
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13. Harkin, S. A.; Jones, R. H.; Tapolczay, D. J.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 1 1989, 489-497. Thomas, E. J.; Whitehead, J. W. F. J. Chem. Soc., Perkin Trans. 1 1989, 499-505. Thomas, E. J.; Whitehead, J. W. F. J. Chem. Soc., Perkin Trans. 1 1989, 507-518. Sauter, R.; Thomas, E. J.; Watts, J. P. J. Chem. Soc., Perkin Trans. 1 1989, 519-523. Merifield, E.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1990, 464-466. Thomas, E. J.; Watts, J. P. J. Chem. Soc., Chem. Commun. 1990, 467-469.
14. Harkin, S. A.; Jones, R. H.; Tapolczay, D. J.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 1 1989, 489-497. Thomas, E. J.; Whitehead, J. W. F. J. Chem. Soc., Perkin Trans. 1 1989, 499-505. Thomas, E. J.; Whitehead, J. W. F. J. Chem. Soc., Perkin Trans. 1 1989, 507-518. Sauter, R.; Thomas, E. J.; Watts, J. P. J. Chem. Soc., Perkin Trans. 1 1989, 519-523. Merifield, E.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1990, 464-466. Thomas, E. J.; Watts, J. P. J. Chem. Soc., Chem. Commun. 1990, 467-469.
15. Harkin, S. A.; Jones, R. H.; Tapolczay, D. J.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 1 1989, 489-497. Thomas, E. J.; Whitehead, J. W. F. J. Chem. Soc., Perkin Trans. 1 1989, 499-505. Thomas, E. J.; Whitehead, J. W. F. J. Chem. Soc., Perkin Trans. 1 1989, 507-518. Sauter, R.; Thomas, E. J.; Watts, J. P. J. Chem. Soc., Perkin Trans. 1 1989, 519-523. Merifield, E.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1990, 464-466. Thomas, E. J.; Watts, J. P. J. Chem. Soc., Chem. Commun. 1990, 467-469.
16. Harkin, S. A.; Jones, R. H.; Tapolczay, D. J.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 1 1989, 489-497. Thomas, E. J.; Whitehead, J. W. F. J. Chem. Soc., Perkin Trans. 1 1989, 499-505. Thomas, E. J.; Whitehead, J. W. F. J. Chem. Soc., Perkin Trans. 1 1989, 507-518. Sauter, R.; Thomas, E. J.; Watts, J. P. J. Chem. Soc., Perkin Trans. 1 1989, 519-523. Merifield, E.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1990, 464-466. Thomas, E. J.; Watts, J. P. J. Chem. Soc., Chem. Commun. 1990, 467-469.
17. Harkin, S. A.; Jones, R. H.; Tapolczay, D. J.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 1 1989, 489-497. Thomas, E. J.; Whitehead, J. W. F. J. Chem. Soc., Perkin Trans. 1 1989, 499-505. Thomas, E. J.; Whitehead, J. W. F. J. Chem. Soc., Perkin Trans. 1 1989, 507-518. Sauter, R.; Thomas, E. J.; Watts, J. P. J. Chem. Soc., Perkin Trans. 1 1989, 519-523. Merifield, E.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1990, 464-466. Thomas, E. J.; Watts, J. P. J. Chem. Soc., Chem. Commun. 1990, 467-469.
18. For IMDA reactions with trienes, which cyclize spontaneously at room temperature upon oxidation of an allylic alcohol to the vinyl ketone, see: Taber, D. F.; Gunn, B. P. J. Am. Chem. Soc. 1979, 101, 3992-3993. Gras, J. L.; Bertrand, M. Tetrahedron Lett. 1979, 20, 7301-7304. Vig, O. P.; Trehan, I. R.; Kumar, R. J. Chem. Ind. 1977, 15B, 319-322. Vig, O. P.; Trehan, I. R.; Malik, N.; Kumar, R. J. Chem. Ind. 1978, 16B, 449-451. For a related reaction, see: Oppolzer, W.; Snowdon, R. L. Tetrahedron Lett. 1976, 17, 4187-4190.
19. For IMDA reactions with trienes, which cyclize spontaneously at room temperature upon oxidation of an allylic alcohol to the vinyl ketone, see: Taber, D. F.; Gunn, B. P. J. Am. Chem. Soc. 1979, 101, 3992-3993. Gras, J. L.; Bertrand, M. Tetrahedron Lett. 1979, 20, 7301-7304. Vig, O. P.; Trehan, I. R.; Kumar, R. J. Chem. Ind. 1977, 15B, 319-322. Vig, O. P.; Trehan, I. R.; Malik, N.; Kumar, R. J. Chem. Ind. 1978, 16B, 449-451. For a related reaction, see: Oppolzer, W.; Snowdon, R. L. Tetrahedron Lett. 1976, 17, 4187-4190.
20. For IMDA reactions with trienes, which cyclize spontaneously at room temperature upon oxidation of an allylic alcohol to the vinyl ketone, see: Taber, D. F.; Gunn, B. P. J. Am. Chem. Soc. 1979, 101, 3992-3993. Gras, J. L.; Bertrand, M. Tetrahedron Lett. 1979, 20, 7301-7304. Vig, O. P.; Trehan, I. R.; Kumar, R. J. Chem. Ind. 1977, 15B, 319-322. Vig, O. P.; Trehan, I. R.; Malik, N.; Kumar, R. J. Chem. Ind. 1978, 16B, 449-451. For a related reaction, see: Oppolzer, W.; Snowdon, R. L. Tetrahedron Lett. 1976, 17, 4187-4190.
21. For IMDA reactions with trienes, which cyclize spontaneously at room temperature upon oxidation of an allylic alcohol to the vinyl ketone, see: Taber, D. F.; Gunn, B. P. J. Am. Chem. Soc. 1979, 101, 3992-3993. Gras, J. L.; Bertrand, M. Tetrahedron Lett. 1979, 20, 7301-7304. Vig, O. P.; Trehan, I. R.; Kumar, R. J. Chem. Ind. 1977, 15B, 319-322. Vig, O. P.; Trehan, I. R.; Malik, N.; Kumar, R. J. Chem. Ind. 1978, 16B, 449-451. For a related reaction, see: Oppolzer, W.; Snowdon, R. L. Tetrahedron Lett. 1976, 17, 4187-4190.
22. For IMDA reactions with trienes, which cyclize spontaneously at room temperature upon oxidation of an allylic alcohol to the vinyl ketone, see: Taber, D. F.; Gunn, B. P. J. Am. Chem. Soc. 1979, 101, 3992-3993. Gras, J. L.; Bertrand, M. Tetrahedron Lett. 1979, 20, 7301-7304. Vig, O. P.; Trehan, I. R.; Kumar, R. J. Chem. Ind. 1977, 15B, 319-322. Vig, O. P.; Trehan, I. R.; Malik, N.; Kumar, R. J. Chem. Ind. 1978, 16B, 449-451. For a related reaction, see: Oppolzer, W.; Snowdon, R. L. Tetrahedron Lett. 1976, 17, 4187-4190.
23. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156. Boeckman, R. J. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1995; Vol. 7, pp. 4982-4987, and references cited therein. Speicher, A.; Bomm, V.; Eicher, T. J. Prakt. Chemie 1996, 338, 588-590.
24. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156. Boeckman, R. J. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1995; Vol. 7, pp. 4982-4987, and references cited therein. Speicher, A.; Bomm, V.; Eicher, T. J. Prakt. Chemie 1996, 338, 588-590.
25. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156. Boeckman, R. J. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1995; Vol. 7, pp. 4982-4987, and references cited therein. Speicher, A.; Bomm, V.; Eicher, T. J. Prakt. Chemie 1996, 338, 588-590.