New tandem Zn-promoted brook rearrangement/ene-allene carbocyclization reactions

Organic Letters

Volumn 7, Issue 23, 2005, Pages 5313-5316

  Unger, Rozalia ^a   Cohen, Theodore ^b   Marek, Ilan ^a  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

^b UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 28244469271     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052237b     Document Type: Article

References (41)

1. (a) Brook, A. G. J. Am. Chem. Soc. 1958, 80, 1886.
2. (b) Brook, A. G.; Warner, C. M.; McGriksin, M. E. J. Am. Chem. Soc. 1959, 81, 981.
3. (c) Brook, A. G.; Schwartz, N. V. J. Am. Chem. Soc. 1960, 82, 2435.
4. (d) Brook, A. G.; Ischia, B. J. Am. Chem. Soc. 1961, 83, 827.
5. (e) Brook, A. G. Acc. Chem. Res. 1974, 7, 77.
6. West, R.; Lowe, R.; Stewart, H. F.; Wright, A. J. Am. Chem. Soc. 1971, 93, 282.
7. (a) Leroux, F.; Schlosser, M.; Zohar, E.; Marek, I. In The Preparation of Organolithium Reagents and Intermediates in The Chemistry of Organolithium Compounds; Rappoport, Z., Marek, I., Eds.; Wiley: Chichester, 2004; p 435.
8. (b) Moser, W. H. Tetrahedron 2001, 57, 2065.
9. 3Li-LiBr complex; in the absence of lithium halide, only mixtures of oligomeric products are obtained. See ref 6a.
10. Reich, H. J.; Olson, R. E.; Clark, M. C. J. Am. Chem. Soc. 1980, 102, 1423.
11. For representative examples, see: (a) Reich, H. J.; Eisenhart, E. K.; Olson, R. E.; Kelly, M. J. J. Am. Chem. Soc. 1986, 108, 7791.
12. (b) Reich, H. J.; Holtan, R. C.; Bolm, C. J. Am. Chem. Soc. 1990, 112, 5609.
13. (c) Reich, H. J.; Kelly, M. J. J. Am. Chem. Soc. 1982, 104, 1119.
14. (d) Reich, H. J.; Kelly, M. J.; Olson, R. E.; Holtan, R. C. Tetrahedron 1983, 39, 949.
15. (a) Sklute, G.; Amsallem, D.; Shibli, A.; Varghese, J. P.; Marek, I. J. Am. Chem. Soc. 2003, 125, 11776.
16. (b) Varghese, J. P.; Zouev, I.; Aufauvre, L.; Knochel, P.; Marek, I. Eur. J. Org. Chem. 2002, 4151.
17. (c) Deng, K.; Chalker, J.; Yang, A.; Cohen, T. Org. Lett. 2005, 7, 3637.
18. (d) Klein, S.; Marek, I.; Normant, J. F. J. Org. Chem. 1994, 59, 2925.
19. (e) Norsikian, S.; Marek, I.; Klein, S.; Poisson, J. F.; Normant, J. F. Chem. Eur. J. 1999, 5, 2055.
20. (f) Marek, I. Tetrahedron 2002, 58, 9463.
21. If alkynyllithium derivatives are used, the Brook rearrangement is much slower even after the addition of zinc salt. This effect is not clearly understood, but the combination magnesium halide/zinc salt exerts an influence on the rate and equilibrium of the C to O silyl rearrangement. Without zinc salt, no rearrangement of the magnesium alcoholate was detected.
22. No attempts were made to isolate its siloxyallenyl precursor.
23. Lange's Handbook of Chemistry, 15th ed. (on line); Dean, J. A., Ed.; McGraw-Hill: New York, 1999.
24. The products of electrophilic capture of propargylic/allenic organozincs can be explained by assuming that the equilibria between propargylzincs and allenylzincs lie far in favor of the latter, (a) Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565.
25. (b) Poisson, J. F.; Normant, J. F. J. Am. Chem. Soc. 2001, 123, 4639.
26. (c) Lorthiois, E.; Marek, I.; Normant, J. F. Tetrahedron Lett. 1996, 37, 6693.
27. (d) Lorthiois, E.; Marek, I.; Meyer, C.; Normant, J. F. Tetrahedron Lett. 1996, 37, 6689.
28. (e) Poisson, J. F.; Chemla, F.; Normant, J. F. Synlett. 2001, 305.
29. (f) Poisson, J. F.; Normant, J. F. J. Org. Chem. 2000, 65, 6553.
30. (g) Harada, T.; Katsuhira, T.; Osada, A.; Iwazaki, K.; Maejima, K.; Oku, A. J. Am. Chem. Soc. 1996, 118, 11377.
31. (a) Meyer, C.; Marek, I.; Normant, J. F.; Platzer, N. Tetrahedron Lett. 1994, 35, 5645.
32. (b) Meyer, C.; Marek, I.; Courtemanche, G.; Normant, J. F. J. Org. Chem. 1995, 60, 863.
33. (c) Lorthiois, E.; Marek, I.; Meyer, C.; Normant, J. F. Tetrahedron Lett. 1995, 36, 1263.
34. (d) Meyer, C.; Marek, I.; Normant, J. F. Tetrahedron Lett. 1996, 37, 857.
35. (e) Lorthiois, E.; Marek, I.; Normant, J. F. Tetrahedron Lett. 1997, 38, 89.
36. (f) Lorthiois, E.; Marek, I.; Normant, J. F. Bull. Chem. Soc. Fr. 1997, 134, 333.
37. Courtemanche, G.; Normant, J. F. Tetrahedron Lett. 1991, 32, 5317.
38. The carbocyclization reaction to 19c was incomplete leading to the isolation of the hydrolysis product of 17c.
39. (a) Battioni, J. P.; Capmau, M. L.; Chodkiewicz, W. Bull. Soc. Chim. Fr. 1969, 3, 976.
40. (b) Battioni, J. P.; Chodkiewicz, W. Bull. Soc. Chim. Fr. 1969, 3, 981.
41. (c) Cannone, P.; Bernatchez, M. J. Org. Chem. 1986, 57, 2147.