Synthetic Applications of a Novel Pericyclic Imino Ene Reaction of Allenyl Silanes

Journal of Heterocyclic Chemistry

Volumn 33, Issue 5, 1996, Pages 1429-1436

  Weinreb, Steven M ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005812861     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570330502     Document Type: Article

References (46)

1. B. J. Baker, P. J. Scheuer and J. N. Shoolery, J. Am. Chem. Soc., 110, 965 (1988).
2. E. Fahy, T. F. Molinski, M. K. Harper, B. W. Sullivan, D. J. Faulkner, L. Parkany and J. Clardy, Tetrahedron Lett., 29, 3427 (1988).
3. For a preliminary account of this work, see: R. M. Borzilleri, S. M. Weinreb and M. Parvez, J. Am. Chem. Soc., 116, 9789 (1994).
4. A. G. M. Barrett, M. L. Boys and T. L. Boehm, J. Chem. Soc., Chem. Commun., 1881 (1994).
5. [a] R. L. Danheiser and D. J. Carini, J. Org. Chem., 45, 3925 (1980);
6. [b] R. L. Danheiser, D. J. Carini and C. A. Kwasigroch, J. Org. Chem., 51, 3870 (1986);
7. [c] R. L. Danheiser, C. A. Kwasigroch and Y.-M. Tsai, J. Am. Chem. Soc., 107, 7233 (1985);
8. [d] R. L. Danheiser, E. J. Stoner, H. Koyama, D. S. Yamashita and C. A. Klade, J. Am. Chem. Soc., 111, 4407 (1989);
9. [e] D. A. Becker and R. L. Danheiser, J. Am. Chem. Soc., 111, 389 (1989).
10. For a preliminary description of these model studies, see: J. Jin, D. T. Smith and S. M. Weinreb, J. Org. Chem., 60, 5366 (1995).
11. R. E. Claus and S. L. Schreiber, Org. Synth., 64, 150 (1984).
12. 2′-anti process.
13. For a review of the imino ene reaction, see: R. M. Borzilleri and S. M. Weinreb, Synthesis, 347 (1995).
14. J. B. Lambert, Tetrahedron Rep., 46, 2677 (1990).
15. For a review of the carbonyl ene reaction, see: B. B. Snider, "The Prins and Carbonyl Ene Reactions," In Comprehensive Organic Synthesis; B. M. Trost, ed., Pergamon Press: Oxford, 1991, Vol. 2, p. 57.
16. For reviews of the all carbon ene reaction, see: [a] B.B. Snider, "Ene Reactions with Alkenes as Enophiles," In Comprehensive Organic Synthesis; B. M. Trost, ed., Pergamon Press: Oxford, 1991, Vol. 5, p. 1; [b] K. Mikami and M. Shimizu, Chem. Rev., 92, 1021 (1992); [c] W. Oppolzer, Angew. Chem., Int. Ed. Engl., 23, 876 (1984).
17. For reviews of the all carbon ene reaction, see: [a] B.B. Snider, "Ene Reactions with Alkenes as Enophiles," In Comprehensive Organic Synthesis; B. M. Trost, ed., Pergamon Press: Oxford, 1991, Vol. 5, p. 1; [b] K. Mikami and M. Shimizu, Chem. Rev., 92, 1021 (1992); [c] W. Oppolzer, Angew. Chem., Int. Ed. Engl., 23, 876 (1984).
18. For reviews of the all carbon ene reaction, see: [a] B.B. Snider, "Ene Reactions with Alkenes as Enophiles," In Comprehensive Organic Synthesis; B. M. Trost, ed., Pergamon Press: Oxford, 1991, Vol. 5, p. 1; [b] K. Mikami and M. Shimizu, Chem. Rev., 92, 1021 (1992); [c] W. Oppolzer, Angew. Chem., Int. Ed. Engl., 23, 876 (1984).
19. W. D. Huntsman, Y. Li and V. P. Giannamore, Isr. J. Chem., 26, 88 (1985).
20. S. Kobayashi, K. Kamiyama and M. Ohno, Chem. Pharm. Bull., 38, 350 (1990).
21. L. A. Paquette and N. A. Nelson, J. Org. Chem., 27, 2272 (1962).
22. The enantiomer of lactone 42 could be prepared by diborane reduction of the carboxylic acid group of 41.
23. We are grateful to Dr. M. Parvez, University of Calgary, for X-ray structure determinations.
24. D. DiPietro, R. M. Borzilleri and S. M. Weinreb, J. Org. Chem., 59, 5856 (1994).
25. H. X. Zhang, F. Guibe and G. Balavoine, J. Org. Chem., 55, 1857 (1990).
26. S. Ghosal, G. P. Luke and K. S. Kyler, J. Org. Chem., 52, 4296 (1987).
27. R. M. Borzilleri, Ph.D. Thesis, The Pennsylvania State University (1994).
28. M. E. Jung and L. A. Light, Tetrahedron Lett., 23, 3851 (1982); G. A. Tolstikov, M. S. Miftakhov, N. A. Danilova and Y. L. Vel'der, Synthesis, 496 (1986).
29. M. E. Jung and L. A. Light, Tetrahedron Lett., 23, 3851 (1982); G. A. Tolstikov, M. S. Miftakhov, N. A. Danilova and Y. L. Vel'der, Synthesis, 496 (1986).
30. S. Kanemoto, S. Matsubara, K. Oshima, K. Utimoto and H. Nozaki, Chemistry Lett., 5 (1987). L. S. Liebeskind and S. W. Riesinger, Tetrahedron Lett., 32, 5681 (1991).
31. S. Kanemoto, S. Matsubara, K. Oshima, K. Utimoto and H. Nozaki, Chemistry Lett., 5 (1987). L. S. Liebeskind and S. W. Riesinger, Tetrahedron Lett., 32, 5681 (1991).
32. 1H NMR spectra of of natural (-)-papuamine (1) and its hydrochloride.
33. For reviews, see: S. F. Martin, "The Amaryllidaceae Alkaloids," In The Alkaloids, A. Brossi, ed., Academic Press, San Diego, 1987, Vol. 30, p. 252. J. R. Lewis, Nat. Prod. Rep., 10, 291 (1993).
34. For reviews, see: S. F. Martin, "The Amaryllidaceae Alkaloids," In The Alkaloids, A. Brossi, ed., Academic Press, San Diego, 1987, Vol. 30, p. 252. J. R. Lewis, Nat. Prod. Rep., 10, 291 (1993).
35. M. Ishizaki, O. Hoshino and Y. Iitaka, J. Org. Chem., 57, 7285 (1992) and references cited therein.
36. L. E. Overman and J. Shim, J. Org. Chem., 58, 4662 (1993) and references cited therein.
37. S. L. Schreiber, T. L. Schreiber and D. B. Smith, J. Am. Chem. Soc., 109, 1525 (1987).
38. C. H. Behrens, S. Y. Ko, K. B. Sharpless and F. J. Walker, J. Org. Chem., 50, 5687 (1985).
39. G. W. Kabalka and H. C. Hedgecock, Jr., J. Org. Chem., 40, 1776 (1975). H. C. Brown, S. U. Kulkarni and C. G. Rao, Synthesis, 151 (1980).
40. G. W. Kabalka and H. C. Hedgecock, Jr., J. Org. Chem., 40, 1776 (1975). H. C. Brown, S. U. Kulkarni and C. G. Rao, Synthesis, 151 (1980).
41. R. S. Brinkmeyer and V. M. Kapoor, J. Am. Chem. Soc., 99, 8339 (1977). N. Cohen, R. J. Lopresti, C. Neukom and G. Saucy, J. Org. Chem., 45, 583 (1980).
42. R. S. Brinkmeyer and V. M. Kapoor, J. Am. Chem. Soc., 99, 8339 (1977). N. Cohen, R. J. Lopresti, C. Neukom and G. Saucy, J. Org. Chem., 45, 583 (1980).
43. P. M. Wovkulich, K. Shankaran, J. Kiegiel and M. R. Uskokovic, J. Org. Chem., 58, 832 (1993).
44. Direct reaction of aldehyde 85 with o-bromopiperonyl amine to produce the imine failed. Under forcing conditions, only the α,β-unsaturated aldehyde formed by β-elimination of siloxy aldehyde 85 was produced.
45. cf. P. H. Lambert, M. Vaultier and R. Carrie, J. Chem. Soc., Chem. Commun., 1224 (1982) and references cited therein.
46. R. F. Heck, Org. React., 27, 345 (1982).