Preparation and Diels-Alder Reactivity of 1-Amino-3-siloxy-1,3-butadienes

Journal of Organic Chemistry

Volumn 62, Issue 16, 1997, Pages 5252-5253

  Kozmin, Sergey A ^a   Rawal, Viresh H ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000123574     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970438q     Document Type: Article

References (31)

1. Oppolzer, W. Intermolecular Diels-Alder Reactions. In Comprehensive Organic Synthesis; Pergamon Press: New York, 1991; Vol 5, pp 315-400.
2. (a) Petrzilka, M.; Grayson, J. I. Synthesis 1981, 753.
3. (b) Fringuelli, F.; Taticchi, A. Dienes in the Diels-Alder Reaction; Wiley: New York, 1990.
4. (a) Shavrygina, O. A., Makin, S. M. Khim-Farm. Zh. 1969, 3, 17.
5. (b) Cazeau, P., Frainnet, E. Bull. Soc. Chim. Fr. 1972, 1658-1659.
6. (c) Jung, M. E., McCombs, C. A. Tetrrahedron Lett. 1976, 2935-2938.
7. (d) Ibuka, T., Mori, Y., Inubushi, Y. Tetrrahedron Lett. 1976, 3169-3172.
8. (e) Obrecht, D. Helv. Chim. Acta 1991, 74, 27-46.
9. Reviews: (a) Danishefsky, S. Acc. Chem. Res. 1981, 14, 400. (b) Danishefsky, S. J.; DeNinno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15. (c) Danishefsky, S. Chemtracts-Org. Chem. 1989, 2, 273.
10. Reviews: (a) Danishefsky, S. Acc. Chem. Res. 1981, 14, 400. (b) Danishefsky, S. J.; DeNinno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15. (c) Danishefsky, S. Chemtracts-Org. Chem. 1989, 2, 273.
11. Reviews: (a) Danishefsky, S. Acc. Chem. Res. 1981, 14, 400. (b) Danishefsky, S. J.; DeNinno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15. (c) Danishefsky, S. Chemtracts-Org. Chem. 1989, 2, 273.
12. For a review on 2-amino dienes, see: (a) Enders, D.; Meyer, O. Liebigs. Ann. 1996, 1023. For the preparation and use of 1-amino dienes, see: (b) Oppolzer, W.; Frostl, W. Helv. Chim. Acta 1975, 58, 590. (c) Oppolzer, W.; Bieber, L.; Francotte, E. Tetrahedron Lett. 1979, 4537. (d) Overman, L. E.; Taylor, G. F.; Jessup, P. J. Tetrahedron Lett. 1976, 3089. (e) Overman, L. E.; Jessup, P. J. J. Am. Chem. Soc. 1978, 100, 5179. (f) Overman, L. E.; Freerks, R. L.; Petty, C. B.; Clizbe, L. A.; Ono, R. K.; Taylor, G. F.; Jessup, P. J. J. Am. Chem. Soc. 1981, 103, 2817. (g) Sustmann, R.; Rogge, M.; Nuchter, U.; Bandmann, H. Chem. Ber. 1992, 125, 1647, and references cited therein.
13. For a review on 2-amino dienes, see: (a) Enders, D.; Meyer, O. Liebigs. Ann. 1996, 1023. For the preparation and use of 1-amino dienes, see: (b) Oppolzer, W.; Frostl, W. Helv. Chim. Acta 1975, 58, 590. (c) Oppolzer, W.; Bieber, L.; Francotte, E. Tetrahedron Lett. 1979, 4537. (d) Overman, L. E.; Taylor, G. F.; Jessup, P. J. Tetrahedron Lett. 1976, 3089. (e) Overman, L. E.; Jessup, P. J. J. Am. Chem. Soc. 1978, 100, 5179. (f) Overman, L. E.; Freerks, R. L.; Petty, C. B.; Clizbe, L. A.; Ono, R. K.; Taylor, G. F.; Jessup, P. J. J. Am. Chem. Soc. 1981, 103, 2817. (g) Sustmann, R.; Rogge, M.; Nuchter, U.; Bandmann, H. Chem. Ber. 1992, 125, 1647, and references cited therein.
14. For a review on 2-amino dienes, see: (a) Enders, D.; Meyer, O. Liebigs. Ann. 1996, 1023. For the preparation and use of 1-amino dienes, see: (b) Oppolzer, W.; Frostl, W. Helv. Chim. Acta 1975, 58, 590. (c) Oppolzer, W.; Bieber, L.; Francotte, E. Tetrahedron Lett. 1979, 4537. (d) Overman, L. E.; Taylor, G. F.; Jessup, P. J. Tetrahedron Lett. 1976, 3089. (e) Overman, L. E.; Jessup, P. J. J. Am. Chem. Soc. 1978, 100, 5179. (f) Overman, L. E.; Freerks, R. L.; Petty, C. B.; Clizbe, L. A.; Ono, R. K.; Taylor, G. F.; Jessup, P. J. J. Am. Chem. Soc. 1981, 103, 2817. (g) Sustmann, R.; Rogge, M.; Nuchter, U.; Bandmann, H. Chem. Ber. 1992, 125, 1647, and references cited therein.
15. For a review on 2-amino dienes, see: (a) Enders, D.; Meyer, O. Liebigs. Ann. 1996, 1023. For the preparation and use of 1-amino dienes, see: (b) Oppolzer, W.; Frostl, W. Helv. Chim. Acta 1975, 58, 590. (c) Oppolzer, W.; Bieber, L.; Francotte, E. Tetrahedron Lett. 1979, 4537. (d) Overman, L. E.; Taylor, G. F.; Jessup, P. J. Tetrahedron Lett. 1976, 3089. (e) Overman, L. E.; Jessup, P. J. J. Am. Chem. Soc. 1978, 100, 5179. (f) Overman, L. E.; Freerks, R. L.; Petty, C. B.; Clizbe, L. A.; Ono, R. K.; Taylor, G. F.; Jessup, P. J. J. Am. Chem. Soc. 1981, 103, 2817. (g) Sustmann, R.; Rogge, M.; Nuchter, U.; Bandmann, H. Chem. Ber. 1992, 125, 1647, and references cited therein.
16. For a review on 2-amino dienes, see: (a) Enders, D.; Meyer, O. Liebigs. Ann. 1996, 1023. For the preparation and use of 1-amino dienes, see: (b) Oppolzer, W.; Frostl, W. Helv. Chim. Acta 1975, 58, 590. (c) Oppolzer, W.; Bieber, L.; Francotte, E. Tetrahedron Lett. 1979, 4537. (d) Overman, L. E.; Taylor, G. F.; Jessup, P. J. Tetrahedron Lett. 1976, 3089. (e) Overman, L. E.; Jessup, P. J. J. Am. Chem. Soc. 1978, 100, 5179. (f) Overman, L. E.; Freerks, R. L.; Petty, C. B.; Clizbe, L. A.; Ono, R. K.; Taylor, G. F.; Jessup, P. J. J. Am. Chem. Soc. 1981, 103, 2817. (g) Sustmann, R.; Rogge, M.; Nuchter, U.; Bandmann, H. Chem. Ber. 1992, 125, 1647, and references cited therein.
17. For a review on 2-amino dienes, see: (a) Enders, D.; Meyer, O. Liebigs. Ann. 1996, 1023. For the preparation and use of 1-amino dienes, see: (b) Oppolzer, W.; Frostl, W. Helv. Chim. Acta 1975, 58, 590. (c) Oppolzer, W.; Bieber, L.; Francotte, E. Tetrahedron Lett. 1979, 4537. (d) Overman, L. E.; Taylor, G. F.; Jessup, P. J. Tetrahedron Lett. 1976, 3089. (e) Overman, L. E.; Jessup, P. J. J. Am. Chem. Soc. 1978, 100, 5179. (f) Overman, L. E.; Freerks, R. L.; Petty, C. B.; Clizbe, L. A.; Ono, R. K.; Taylor, G. F.; Jessup, P. J. J. Am. Chem. Soc. 1981, 103, 2817. (g) Sustmann, R.; Rogge, M.; Nuchter, U.; Bandmann, H. Chem. Ber. 1992, 125, 1647, and references cited therein.
18. For a review on 2-amino dienes, see: (a) Enders, D.; Meyer, O. Liebigs. Ann. 1996, 1023. For the preparation and use of 1-amino dienes, see: (b) Oppolzer, W.; Frostl, W. Helv. Chim. Acta 1975, 58, 590. (c) Oppolzer, W.; Bieber, L.; Francotte, E. Tetrahedron Lett. 1979, 4537. (d) Overman, L. E.; Taylor, G. F.; Jessup, P. J. Tetrahedron Lett. 1976, 3089. (e) Overman, L. E.; Jessup, P. J. J. Am. Chem. Soc. 1978, 100, 5179. (f) Overman, L. E.; Freerks, R. L.; Petty, C. B.; Clizbe, L. A.; Ono, R. K.; Taylor, G. F.; Jessup, P. J. J. Am. Chem. Soc. 1981, 103, 2817. (g) Sustmann, R.; Rogge, M.; Nuchter, U.; Bandmann, H. Chem. Ber. 1992, 125, 1647, and references cited therein.
19. (a) Smith, A. B., III; Wexler, B. A.; Tu, C.-Y.; Konopelski, J. P. J. Am. Chem. Soc. 1985, 107, 1308, and recerences cited therein.
20. (b) Comins, D. L.; Al-awar, R. S. J. Org. Chem. 1992, 57, 4098.
21. 1-Amino-3-ethoxy-1,3-butadiene was previously prepared but never used in a Diels-Alder reaction: Meerwein, H.; Florian, W.; Schon, N.; Stopp, G. Liebigs Ann. 1961, 641, 1.
22. For a recent review, see: (a) Shiosaki, K. Eschenmoser Coupling Reaction. In Comprehensive Organic Synthesis; Pergamon Press: New York, 1991; Vol 2, pp 865-892. Also, see: (b) Ireland, R. E.; Brown, F. R. J. Org. Chem. 1980, 45, 1868.
23. Also, see: (b) Ireland, R. E.; Brown, F. R. J. Org. Chem. 1980, 45, 1868.
24. (a) Lienhard, U.; Fahrni, H.-P.; Neuenschwander, M. Helv. Chim. Acta 1978, 61, 1609.
25. (b) Markova, N. K.; Zaichenko, Y. A.; Tsil'ko, A. E.; Maretina, I. A. J. Org. Chem. USSR 1984, 876.
26. Other dialkylamino-substituted dienes were similarly prepared. Details of their synthesis and reactivity will be reported in due course.
27. Dienes 3-5 are slowly hydrolyzed in water and in the presence of Lewis acids.
28. Baldwin, S. W.; Greenspan, P.; Alaimo, C.; McPhail, A. T. Tetrahedron Lett. 1991, 32, 5877.
29. Danishefsky, S.; Kitahara, T.; Yan, C. F.; Morris, J. J. Am. Chem. Soc. 1979, 101, 6996.
30. Typical Diets-Alder procedure: To a solution of diene 3 (1.21.5 mmol) in dry toluene (1-2 mL) was added the dienophile (1 mmol), and the reaction mixture was stirred overnight at the temperature indicated (see Table 1). Concentration in vacuo, followed by flash chromotography on silica gel (the eluent contained 2-5% triethylamine), afforded the cycloadducts shown.
31. Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1997, 119, 7165.