Hetero Diels-Alder reactions of 1-amino-3-siloxy-1,3-butadienes under strictly thermal conditions

Organic Letters

Volumn 2, Issue 21, 2000, Pages 3321-3323

  Huang, Yong ^a   Rawal, Viresh H ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE DERIVATIVE; IMINE; KETONE;

ARTICLE; CHEMISTRY; TEMPERATURE;

BUTADIENES; IMINES; KETONES; TEMPERATURE;

EID: 0034687197     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006404d     Document Type: Article

References (28)

1. For excellent general reviews, see: (a) Tietze, L. F.; Kettschau, G. In Topics in Current Chemistry; Metz, P., Ed.; Springer-Verlag: Berlin, 1997; Vol. 189, pp 1-120, and references therein.
2. (b) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Wasserman, H. H., Ed; Academic Press: San Diego, CA, 1987; Vol. 47.
3. Reviews: (a) Schmidt, R. R. Acc. Chem. Res. 1986, 19, 250-259.
4. (b) Danishefsky, S. J.; DeNinno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 15, 5-23.
5. (c) Kametani, T.; Hibino, S. Adv. Heterocycl Chem. 1987, 42, 245-333.
6. (d) Bednarski, M. D.; Lyssikatos, J. P. In Comprehensive Organic Synthesis; Trost, B. M., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 2, pp 661-706.
7. (a) Gresham, T. L.; Steadman, T. R. J. Am. Chem. Soc. 1949, 71, 737-738.
8. (b) Dale, W. J.; Sisti, A. J. J. Am. Chem. Soc. 1954, 76, 81-82.
9. (c) Jung, M. E.; Shishido, K.; Light, L.; Davis, L. Tetrahedron. Lett. 1981, 22, 4607-4610.
10. Jurczak, J.; Chmielewski, M.; Filipek, S. Synthesis 1979, 41-42.
11. Reviews: (a) Santelli, M.; Pons, J, -M. Lewis Acids and Selectivity in Organic Synthesis; CRC Press: Boca Raton, FL, 1996. See also refs 1 and 2.
12. (a) Molander, G. A.; Rzasa, R. M. J. Org. Chem. 2000, 65, 1215-1217 and references therein.
13. For recent examples of chiral Lewis acid-catalyzed hetero Diels-Alder reactions, see: (b) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1997, 38, 2427-2430.
14. (c) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403-406.
15. (d) Yao, S.; Johannsen, M.; Audrain, H.; Hazell, R. G.; Jørgensen, K. A. J. Am. Chem. Soc. 1998, 120, 8599-8605, and references therein.
16. This work was presented at the 219th National Meeting of the American Chemical Society: Huang, Y.; Rawal, V. H. Abstr. Pap. Am. Chem. Soc. 2000, 219, 527-ORGN. After this manuscript was completed and being readied for submission, a paper appeared describing the thermal hetero Diels-Alder reactions of in situ generated ortho-quinodimethanes with carbonyl and imino hetero dienophiles: Hentemann, M. F.; Allen, J. G.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2000, 39, 1937-1940.
17. This work was presented at the 219th National Meeting of the American Chemical Society: Huang, Y.; Rawal, V. H. Abstr. Pap. Am. Chem. Soc. 2000, 219, 527-ORGN. After this manuscript was completed and being readied for submission, a paper appeared describing the thermal hetero Diels-Alder reactions of in situ generated ortho-quinodimethanes with carbonyl and imino hetero dienophiles: Hentemann, M. F.; Allen, J. G.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2000, 39, 1937-1940.
18. (a) Kozmin, S. A.; Rawal, V. H. J. Org. Chem. 1997, 62, 5252-5253.
19. (b) Kozmin, S. A.; Janey, J. M.; Rawal, V. H. J. Org. Chem. 1999, 64, 3039-3052.
20. Application to tabersonine synthesis: Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1998, 120, 13523-13524.
21. (a) Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1997, 119, 7165-7166.
22. (b) Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1999, 121, 9562-9573.
23. Kozmin, S. A.; Green, M. T.; Rawal, V. H. J. Org. Chem. 1999, 64, 8045-8047.
24. Two preparative procedures have been accepted for publication in Organic Syntheses, one for the synthesis of amino-siloxy diene 1a, and the other for the use of this diene in a Diels-Alder reaction: Kozmin, S. A.; He, S.; Rawal, V. H. Org. Svnth. 2000, 78, in press.
25. Cf.: (a) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron. Lett. 1992, 46, 6907-6910.
26. (b) Keck, G. E.; Li, X.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998-5999.
27. Thermal hetero Diels-Alder reactions of doubly activated imines have been reported: (a) Birkinshaw, T. N.; Tabor, A. B.; Holmes, A. B.; Kaye, P.; Mayne, P. M.; Raithby, P. R. J. Chem. Soc., Chem. Commun. 1988, 1599-1601.
28. (b) Birkinshaw, T. N.; Tabor, A. B.; Holmes, A. B.; Raithby, P. R. J. Chem. Soc., Chem. Commun. 1988, 1601-1602.