An anionic condensation and fragmentation approach to substituted 3-pyrrolines

Tetrahedron Letters

Volumn 43, Issue 49, 2002, Pages 8913-8915

  Weeresakare, G Mahika ^b   Xu, Qing ^a   Rainier, Jon D ^b  

^a University of Arizona   (United States)

^b UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; KETONE DERIVATIVE; PYRROLINE DERIVATIVE;

ARTICLE; DIELS ALDER REACTION; FRAGMENTATION REACTION; HYDROLYSIS; MOLECULE; POLYMERIZATION; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0037010779     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02191-3     Document Type: Article

References (25)

1. Selected recent examples of pyrroline synthesis: (a) Hercouet, A.; Neu, A.; Peyronel, J. F.; Carboni, B. Synlett. 2002, 829; (b) Green, M. P.; Prodger, J. C.; Sherlock, A. E.; Hayes, C. J. Org. Lett. 2001, 3, 3377; (c) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855; (c) Breuil-Desvergnes, V.; Compain, P.; Vatèle, J.-M.; Goré, J. Tetrahedron Lett. 1999, 40, 5009; (d) Ishii, K.; Ohno, H.; Takemoto, Y.; Ibuka, T. Synlett. 1999, 228; (e) Schumacher, K. K.; Jiang, J.; Joullié, M. M.; Tetrahedron: Asymmetry 1998, 9, 47; (f) Ojima, I.; Zhu, J. W.; Vidal, E. S.; Kass, D. F. J. Am. Chem. Soc. 1998, 120, 6690; (g) Balasubramanian, T.; Hassner, A. Tetrahedron Lett. 1996, 37, 5755; (h) Burley, I.; Hewson, A. T. Tetrahedron Lett. 1994, 35, 7099.
2. Selected recent examples of pyrroline synthesis: (a) Hercouet, A.; Neu, A.; Peyronel, J. F.; Carboni, B. Synlett. 2002, 829; (b) Green, M. P.; Prodger, J. C.; Sherlock, A. E.; Hayes, C. J. Org. Lett. 2001, 3, 3377; (c) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855; (c) Breuil-Desvergnes, V.; Compain, P.; Vatèle, J.-M.; Goré, J. Tetrahedron Lett. 1999, 40, 5009; (d) Ishii, K.; Ohno, H.; Takemoto, Y.; Ibuka, T. Synlett. 1999, 228; (e) Schumacher, K. K.; Jiang, J.; Joullié, M. M.; Tetrahedron: Asymmetry 1998, 9, 47; (f) Ojima, I.; Zhu, J. W.; Vidal, E. S.; Kass, D. F. J. Am. Chem. Soc. 1998, 120, 6690; (g) Balasubramanian, T.; Hassner, A. Tetrahedron Lett. 1996, 37, 5755; (h) Burley, I.; Hewson, A. T. Tetrahedron Lett. 1994, 35, 7099.
3. Selected recent examples of pyrroline synthesis: (a) Hercouet, A.; Neu, A.; Peyronel, J. F.; Carboni, B. Synlett. 2002, 829; (b) Green, M. P.; Prodger, J. C.; Sherlock, A. E.; Hayes, C. J. Org. Lett. 2001, 3, 3377; (c) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855; (c) Breuil-Desvergnes, V.; Compain, P.; Vatèle, J.-M.; Goré, J. Tetrahedron Lett. 1999, 40, 5009; (d) Ishii, K.; Ohno, H.; Takemoto, Y.; Ibuka, T. Synlett. 1999, 228; (e) Schumacher, K. K.; Jiang, J.; Joullié, M. M.; Tetrahedron: Asymmetry 1998, 9, 47; (f) Ojima, I.; Zhu, J. W.; Vidal, E. S.; Kass, D. F. J. Am. Chem. Soc. 1998, 120, 6690; (g) Balasubramanian, T.; Hassner, A. Tetrahedron Lett. 1996, 37, 5755; (h) Burley, I.; Hewson, A. T. Tetrahedron Lett. 1994, 35, 7099.
4. Selected recent examples of pyrroline synthesis: (a) Hercouet, A.; Neu, A.; Peyronel, J. F.; Carboni, B. Synlett. 2002, 829; (b) Green, M. P.; Prodger, J. C.; Sherlock, A. E.; Hayes, C. J. Org. Lett. 2001, 3, 3377; (c) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855; (c) Breuil-Desvergnes, V.; Compain, P.; Vatèle, J.-M.; Goré, J. Tetrahedron Lett. 1999, 40, 5009; (d) Ishii, K.; Ohno, H.; Takemoto, Y.; Ibuka, T. Synlett. 1999, 228; (e) Schumacher, K. K.; Jiang, J.; Joullié, M. M.; Tetrahedron: Asymmetry 1998, 9, 47; (f) Ojima, I.; Zhu, J. W.; Vidal, E. S.; Kass, D. F. J. Am. Chem. Soc. 1998, 120, 6690; (g) Balasubramanian, T.; Hassner, A. Tetrahedron Lett. 1996, 37, 5755; (h) Burley, I.; Hewson, A. T. Tetrahedron Lett. 1994, 35, 7099.
5. Selected recent examples of pyrroline synthesis: (a) Hercouet, A.; Neu, A.; Peyronel, J. F.; Carboni, B. Synlett. 2002, 829; (b) Green, M. P.; Prodger, J. C.; Sherlock, A. E.; Hayes, C. J. Org. Lett. 2001, 3, 3377; (c) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855; (c) Breuil-Desvergnes, V.; Compain, P.; Vatèle, J.-M.; Goré, J. Tetrahedron Lett. 1999, 40, 5009; (d) Ishii, K.; Ohno, H.; Takemoto, Y.; Ibuka, T. Synlett. 1999, 228; (e) Schumacher, K. K.; Jiang, J.; Joullié, M. M.; Tetrahedron: Asymmetry 1998, 9, 47; (f) Ojima, I.; Zhu, J. W.; Vidal, E. S.; Kass, D. F. J. Am. Chem. Soc. 1998, 120, 6690; (g) Balasubramanian, T.; Hassner, A. Tetrahedron Lett. 1996, 37, 5755; (h) Burley, I.; Hewson, A. T. Tetrahedron Lett. 1994, 35, 7099.
6. Selected recent examples of pyrroline synthesis: (a) Hercouet, A.; Neu, A.; Peyronel, J. F.; Carboni, B. Synlett. 2002, 829; (b) Green, M. P.; Prodger, J. C.; Sherlock, A. E.; Hayes, C. J. Org. Lett. 2001, 3, 3377; (c) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855; (c) Breuil-Desvergnes, V.; Compain, P.; Vatèle, J.-M.; Goré, J. Tetrahedron Lett. 1999, 40, 5009; (d) Ishii, K.; Ohno, H.; Takemoto, Y.; Ibuka, T. Synlett. 1999, 228; (e) Schumacher, K. K.; Jiang, J.; Joullié, M. M.; Tetrahedron: Asymmetry 1998, 9, 47; (f) Ojima, I.; Zhu, J. W.; Vidal, E. S.; Kass, D. F. J. Am. Chem. Soc. 1998, 120, 6690; (g) Balasubramanian, T.; Hassner, A. Tetrahedron Lett. 1996, 37, 5755; (h) Burley, I.; Hewson, A. T. Tetrahedron Lett. 1994, 35, 7099.
7. Selected recent examples of pyrroline synthesis: (a) Hercouet, A.; Neu, A.; Peyronel, J. F.; Carboni, B. Synlett. 2002, 829; (b) Green, M. P.; Prodger, J. C.; Sherlock, A. E.; Hayes, C. J. Org. Lett. 2001, 3, 3377; (c) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855; (c) Breuil-Desvergnes, V.; Compain, P.; Vatèle, J.-M.; Goré, J. Tetrahedron Lett. 1999, 40, 5009; (d) Ishii, K.; Ohno, H.; Takemoto, Y.; Ibuka, T. Synlett. 1999, 228; (e) Schumacher, K. K.; Jiang, J.; Joullié, M. M.; Tetrahedron: Asymmetry 1998, 9, 47; (f) Ojima, I.; Zhu, J. W.; Vidal, E. S.; Kass, D. F. J. Am. Chem. Soc. 1998, 120, 6690; (g) Balasubramanian, T.; Hassner, A. Tetrahedron Lett. 1996, 37, 5755; (h) Burley, I.; Hewson, A. T. Tetrahedron Lett. 1994, 35, 7099.
8. Selected recent examples of pyrroline synthesis: (a) Hercouet, A.; Neu, A.; Peyronel, J. F.; Carboni, B. Synlett. 2002, 829; (b) Green, M. P.; Prodger, J. C.; Sherlock, A. E.; Hayes, C. J. Org. Lett. 2001, 3, 3377; (c) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855; (c) Breuil-Desvergnes, V.; Compain, P.; Vatèle, J.-M.; Goré, J. Tetrahedron Lett. 1999, 40, 5009; (d) Ishii, K.; Ohno, H.; Takemoto, Y.; Ibuka, T. Synlett. 1999, 228; (e) Schumacher, K. K.; Jiang, J.; Joullié, M. M.; Tetrahedron: Asymmetry 1998, 9, 47; (f) Ojima, I.; Zhu, J. W.; Vidal, E. S.; Kass, D. F. J. Am. Chem. Soc. 1998, 120, 6690; (g) Balasubramanian, T.; Hassner, A. Tetrahedron Lett. 1996, 37, 5755; (h) Burley, I.; Hewson, A. T. Tetrahedron Lett. 1994, 35, 7099.
9. Selected recent examples of pyrroline synthesis: (a) Hercouet, A.; Neu, A.; Peyronel, J. F.; Carboni, B. Synlett. 2002, 829; (b) Green, M. P.; Prodger, J. C.; Sherlock, A. E.; Hayes, C. J. Org. Lett. 2001, 3, 3377; (c) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855; (c) Breuil-Desvergnes, V.; Compain, P.; Vatèle, J.-M.; Goré, J. Tetrahedron Lett. 1999, 40, 5009; (d) Ishii, K.; Ohno, H.; Takemoto, Y.; Ibuka, T. Synlett. 1999, 228; (e) Schumacher, K. K.; Jiang, J.; Joullié, M. M.; Tetrahedron: Asymmetry 1998, 9, 47; (f) Ojima, I.; Zhu, J. W.; Vidal, E. S.; Kass, D. F. J. Am. Chem. Soc. 1998, 120, 6690; (g) Balasubramanian, T.; Hassner, A. Tetrahedron Lett. 1996, 37, 5755; (h) Burley, I.; Hewson, A. T. Tetrahedron Lett. 1994, 35, 7099.
10. Rainier J.D., Xu Q. Org. Lett. 1:1999;27.
11. Xu Q., Weeresakare M., Rainier J.D. Tetrahedron. 57:2001;8029.
12. For reviews of pyrroline containing natural products see: (a) Mauger, A. B. J. Nat. Prod. 1996, 59, 1205; (b) Daly, J. W. J. Nat. Prod. 1998, 61, 162.
13. For reviews of pyrroline containing natural products see: (a) Mauger, A. B. J. Nat. Prod. 1996, 59, 1205; (b) Daly, J. W. J. Nat. Prod. 1998, 61, 162.
14. . For a review on the synthesis of 7-azabicyclo[2.2.1]heptenes which includes Diels-Alder approaches see: Chen Z., Trudell M.L. Chem. Rev. 96:1996;1179.
15. Heaton C.D., Noller C.R. J. Am. Chem. Soc. 71:1949;2948.
16. Chamberlain P., Rooney A.E. Tetrahedron Lett. 20:1979;383.
17. Leroy J. Tetrahedron Lett. 33:1992;2969.
18. Zhang C., Trudell M.L. J. Org. Chem. 61:1996;7189.
19. WARNING: Bromoalkyne 4 is a known lachrymator. In addition, the use of 4 has led to painful skin rashes in spite of the use of protective gear and a well ventilated, high flow fume hood.
20. Shen M., Schultz A.G. Tetrahedron Lett. 22:1981;3347.
21. 2.
22. When exposed to the condensation reaction with aldehydes, oxabicyclo[2.2.1]heptenones having substitution at the bridgehead gave much higher yields of dihydrofurans than those lacking substitution. See Ref. 2 .
23. The olefin geometry was determined spectroscopically from the presence (Z-isomer) or lack (E-isomer) of NOEs between the exocyclic vinyl hydrogen and the ethyl ester hydrogens.
24. . As indirect evidence of this mechanism, we have found that 1 undergoes a two-carbon ring expansion reaction when exposed to unsaturated ketones and esters. See Ref. 2b and: Rainier J.D., Xu Q. Org. Lett. 1:1999;1161.
25. +) 398.1815, found 398.1805.