Tandem zirconocene homologation-aldimine allylation

Organic Letters

Volumn 3, Issue 17, 2001, Pages 2773-2776

  Wipf, Peter ^a   Kendall, Christopher ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0001114287     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0163880     Document Type: Article

References (44)

1. For reviews, see: (a) Kleinman, E. F.; Volkmann, R. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 975-1006.
2. (b) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
3. Risen, N.; Arend, M. In Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21b. pp 1894-1907.
4. Bloch, R. Chem. Rev. 1998, 98, 1407.
5. For example, see: (a) Enders, D.; Schankat, J.; Klatt, M. Synlett 1994, 795.
6. (b) Grepioni, F.; Grilli, S.; Martelli, G.; Savoia, D. J. Org. Chem. 1999, 64, 3679.
7. Hyldtoft, L.; Madsen, R. J. Am. Chem. Soc. 2000, 122, 8444.
8. (a) Nakamura, H.; Nakamura, K.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 4242.
9. (b) Nakamura, K.; Nakamura, H.; Yamamoto, Y. J. Org. Chem. 1999, 64, 2614.
10. Fang, F.; Johannsen, M.; Yao, S.; Gathergood, N.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 1999, 64, 4844.
11. Gastner, T.; Ishitani, H.; Akiyama, R.; Kobayashi, S. Angew. Chem., Int. Ed. 2001, 40, 1896.
12. For recent reviews, see: (a) Liard, A.; Kaftanov, J.; Chechik, H.; Farhat, S.; Morlender-Vais, N.; Averbuj, C.; Marek, I. J. Organomet. Chem. 2001, 624, 26.
13. (b) Fletcher, A. J.; Christie, S. D. R. J. Chem. Soc., Perkin Trans. 1 2001, 1.
14. Erker, G. Acc. Chem. Res. 2001, 34, 309.
15. Marek, I. Chem. Rev. 2000, 100, 2887-2900.
16. (e) Takahashi, T.; Kotora, M.; Hara, R.; Xi, Z. Bull. Chem. Soc. Jpn. 1999, 72, 2591.
17. (e) Wipf, P.; Tsuchimoto, T.; Takahashi, H. Pure Appl. Chem. 1999, 71, 415.
18. (a) Wipf, P.; Jahn, H. Tetrahedron 1996, 52, 12853.
19. (b) Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 15, 333.
20. Wipf, P.; Kendall, C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2001, 123, 5122.
21. 2 alone is not sufficient to induce the reaction, in contrast to observations made in ref 6.
22. 2, the diastereomeric ratio is 83:17, at room temperature the ratio is 85:15, and at 0°C the ratio is 86:14.
23. Yamamoto, Y.; Saito, Y.; Maruyama, K. J. Organomet. Chem. 1985, 292, 311.
24. 3N) to yield 71 mg (71%) of 5a and 5b as an 85:15 (separable) mixture of diastereomers.
25. Chemla, F.; Hebbe, V.; Normant, J.-F. Synthesis 2000, 75.
26. (a) Bhagwatheeswaran, H.; Gaur, S. P.; Jain, P. C. Synthesis 1976, 615.
27. (b) Ramage, R.; Hapton, D.; Parrott, M. J.; Kenner, G. W.; Moore, G. A. J. Chem. Soc., Perkin Trans. 1 1984, 1357.
28. Desai, M. C.; Thadeio, P. F.; Lefkowitz, S. L. Tetrahedron Lett. 1993, 34, 5831.
29. 1H NMR spectra for the substituted vinyl proton, relative to the corresponding proton of the syn isomer. The assignment of 7a is still tentative.
30. 2Zn, no imine addition products are formed.
31. 2Zn: however, although the selectivity for the formation of 5a increased to ca. 10:1, the yield dropped to 47%.
32. For precedence for this type of rearrangement, see: (a) Charette, A. B.; Marcoux, J.-F. J. Am. Chem. Soc. 1996, 118, 4539.
33. (b) McWilliams, J. C.; Armstrong, J. D.; Zheng, N.; Bhupathy, M.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1996, 118, 11970.
34. Sidduri, A.; Rozema, M. J.; Knochel, P. J. Org. Chem. 1993, 58, 2694.
35. Shibli, A.; Varghese, J. P.; Knochel, P.; Marek, I. Synlett 2001, 818.
36. For the allylation of imines with zinc reagents, see: Jones, P.; Knochel, P. J. Org. Chem. 1999, 64, 186.
37. See, for example: Lu, W.; Chan, T. H. J. Org. Chem. 2001, 66, 3467 and references therein.
38. Srebnik, M. Tetrahedron Lett. 1991, 22, 2449.
39. (a) Wipf, P.; Ribe, S. J. Org. Chem. 1998, 63, 6454.
40. (b) Wipf, P.; Xu, W.; Takahashi, H.; Jahn, H.; Coish, P. D. G. Pure Appl. Chem. 1997, 69, 639.
41. Wipf, P.; Xu, W. Tetrahedron Lett. 1994, 35, 5197.
42. Takahashi, T.; Kotora, M.; Fischer, R.; Nishihara, Y.; Nakajima, K. J. Am. Chem. Soc. 1995, 117, 11039.
43. Yasuda, H.; Kajihara, Y.; Mashima, K.; Nagasuna, K.; Nakamura, A. Chem. Lett. 1981, 671.
44. 2Zn is added, no addition to the imine is observed.