Hydrozirconation of alkenyloxirane derivatives: Preparation of cycloalkylmethanols

Tetrahedron

Volumn 54, Issue 5-6, 1998, Pages 753-766

  Harada, Susumu ^a   Kowase, Noboru ^a   Tabuchi, Nobuhito ^a   Taguchi, Takeo ^a   Dobashi, Yasuo ^a   Dobashi, Akira ^a   Hanzawa, Yuji ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ETHYLENE OXIDE DERIVATIVE; METHANOL DERIVATIVE;

ARTICLE; CYCLIZATION; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0032576826     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10340-4     Document Type: Article

References (51)

1. 1. For reviews, see: (a) Wipf, P.; Jahn, H. Tetrahedron 1996, 52, 1253.
2. (b) Lipshutz, B. H.; Bhandari, A.; Lindsley, C.; Keil, R.; Wood, M. R. Pure Appl. Chem. 1994, 66, 1493.
3. (c) Wipf, P. Synthesis 1993, 537.
4. (d) Labinger, J. A. In Comprehensive Organic Synthesis; Paquette, L. A. Ed.; Pergamon Press: Oxford, 1991, Vol. 8, p 667.
5. (e) Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 15, 333.
6. (f) Negishi, E.; Takahashi, T. Synthesis 1988, 1.
7. (g) Negishi, E.; Takahashi, T. Aldrichim. Acta 1985, 18, 31.
8. 2. (a) Buchwald, S. L.; La Maire, S. J.; Nielsen, R. B.; Watson, B. T.; King, S. M. Tetrahedron Lett. 1987, 28, 3895.
9. (b) Buchwald, S. L.; La Maire, S. J.; Nielsen, R. B.; Watson, B. T.; King, S. M. Org. Syn. 1993, 71, 77.
10. (c) Negishi, E.; Miller, J. A.; Yoshida, T. Tetrahedron Lett. 1984, 25, 3407.
11. (d) Lipshutz, B. H.; Keil, R.; Ellsworth, E. L. Tetrahedron Lett. 1990, 31, 7257.
12. 3. Preliminary communication, see Harada, S.; Kowase, N.; Taguchi, T.; Hanzawa, Y. Tetrahedron Lett. 1997, 38, 1957.
13. 4. (a) Vincent, P.; Beaucourt, J.-P.; Pichat, L. Tetrahedron Lett. 1982, 23, 63.
14. (b) Schwartz, J.; Loots, M. J.; Kosugim H. J. Am. Chem. Soc. 1980, 102, 1333.
15. (c) Wipf, P.; Smitrovich, J. H. J. Org. Chem. 1991, 56, 6494.
16. (d) Lipshutz, B. H.; Lindsley, C.; Bhandari, A. Tetrahedron Lett. 1994, 35, 4669.
17. 5. Wang, J.-T.; Zhang, Y.-W.; Xu, Y.-M.; Bai, G.-C. Youji Huaxue 1989, 9, 41.
18. 6. For recent examples for the activation of alkylzirconocene chloride by Ag(I) salt, see: (a) Maeta, H., Hashimoto, T.; Hasegawa, T.; Suzuki, K. Tetrahedron Lett. 1992, 33, 5965.
19. (b) Wipf, P.; Xu, W. J. Org. Chem. 1993, 58, 825.
20. (c) Wipf, P.; Xu, W. J. Org. Chem. 1993, 58, 5880. See also ref 1a.
21. 7. For other examples of the cyclopropyl ring formation by the reactions of alkylzirconocenes, see: (a) Takahashi, T.; Xi, Z.; Kotora, M.; Xi, C.; Nakajima, K. Tetrahedron Lett. 1996, 37, 7521.
22. (b) Harris, M. C. J.; Whitby, R. J.; Blagg, J. Tetrahedron Lett. 1995, 36, 4827.
23. (c) Takahashi, T.; Kondakov, D. Y.; Suzuki, N. Tetrahedron Lett. 1993, 34, 6517.
24. (d) Davis, J. M.; Whitby, R. J.; Jaxa-Chamiec, A. Tetrahedron Lett. 1992, 33, 5655.
25. (e) Schwartz, J.; Labinger, J. A. Angew. Chem., Inl. Ed Engl. 1976, 15, 262.
26. 8. (a) Wipf, P.; Sanitrovich, J. H. J. Org. Chem. 1991, 56, 6494.
27. (b) Gibson, T. Organometallics 1987, 6.
28. (c) Annby, U.; Karlsson, S.; Gronowitz, S.; Hallberg, A.; Alvhaell, J.; Svenson, R. Acta Chem. Scand. 1993, 47, 425.
29. 9. (a) Buchwald, S. L.; Nielsen, R. B.; Dewan, J. C. Organometallics 1988, 7, 2324.
30. (b) Hanzawa, Y.; Ito, H.; Taguchi, T. Synlett 1995, 299.
31. 10. (a) Charette, A. B.; Marcoux, J.-F. Synlett 1995, 1197.
32. (b) Motherwell, W. B.; Nutley, C. J. Contemp. Org. Synth. 1994, 1, 219 and the references cited therein.
33. (c) Charette, A. B.; Lebel, H. J. Org. Chem. 1995, 60, 2966.
34. 11. (a) Wipf, P.; Xu, W. Synlett 1992, 718.
35. (b) Zheng, B,; Srebnik, M. Tetrahedron Lett. 1994, 35, 6247.
36. 12. (a) Endo, J.; Koga, N.; Morokuma, K. Organometallics 1993, 12, 2777.
37. (b) Koga, N.; Morokuma, K. Chem. Rev. 1991, 91, 823.
38. 13. Similar discussion has been reported for the diastereoselective radical addition to α,β-unsaturated carbonyl compound. Porter, N. A.; Scott, D. M.; Rosenstein, I. J.; Giese, B.; Veit, A.; Zeit, H. G. J. Am. Chem. Soc. 1991, 113, 1791.
39. 14. The Boltzman population of gauche-1 A conformer for cis-13 is calculated to be 94% at 300 K. In the trans-13, the Boltzman population of gauche-1 C and trans D conformers is calculated to be 90%.
40. 15. (a) Mulzer, J.; Angermann, A.; Münch, W. Liebigs Ann. Chem. 1986, 825.
41. (b) Mulzer, J.; Angermann, A. Tetrahedron Lett. 1983, 24, 2843.
42. 16. Fang, C.; Ogawa, T.; Suemune, H.; Sakai, K. Tetrahedron Asymmetry 1991, 2, 389.
43. 17. cis-10a, d and cis-10f: Hosomi, A.; Kohra, S.; Tominaga, Y.; Ando, M.; Sakurai, H. Chem. Pharm. Bull. 1987, 35, 3058. trans-10a: Julia, M.; Verpeaux, J.-N.; Zahneisen, T. Bull. Soc. Chim. Fr. 1994, 131, 539. 10c: Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1995, 117, 7379. 10e: Oshima, M.; Yamazaki, H.; Shimizu, I.; Nisar, M.; Tsuji, J. J. Am. Chem. Soc. 1989, 111, 6280.
44. 17. cis-10a, d and cis-10f: Hosomi, A.; Kohra, S.; Tominaga, Y.; Ando, M.; Sakurai, H. Chem. Pharm. Bull. 1987, 35, 3058. trans-10a: Julia, M.; Verpeaux, J.-N.; Zahneisen, T. Bull. Soc. Chim. Fr. 1994, 131, 539. 10c: Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1995, 117, 7379. 10e: Oshima, M.; Yamazaki, H.; Shimizu, I.; Nisar, M.; Tsuji, J. J. Am. Chem. Soc. 1989, 111, 6280.
45. 17. cis-10a, d and cis-10f: Hosomi, A.; Kohra, S.; Tominaga, Y.; Ando, M.; Sakurai, H. Chem. Pharm. Bull. 1987, 35, 3058. trans-10a: Julia, M.; Verpeaux, J.-N.; Zahneisen, T. Bull. Soc. Chim. Fr. 1994, 131, 539. 10c: Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1995, 117, 7379. 10e: Oshima, M.; Yamazaki, H.; Shimizu, I.; Nisar, M.; Tsuji, J. J. Am. Chem. Soc. 1989, 111, 6280.
46. 17. cis-10a, d and cis-10f: Hosomi, A.; Kohra, S.; Tominaga, Y.; Ando, M.; Sakurai, H. Chem. Pharm. Bull. 1987, 35, 3058. trans-10a: Julia, M.; Verpeaux, J.-N.; Zahneisen, T. Bull. Soc. Chim. Fr. 1994, 131, 539. 10c: Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1995, 117, 7379. 10e: Oshima, M.; Yamazaki, H.; Shimizu, I.; Nisar, M.; Tsuji, J. J. Am. Chem. Soc. 1989, 111, 6280.
47. 18. Ipaktschi, J.; Heydari, A.; Kalinnowski, H.-O. Chem. Ber. 1994, 127, 905.
48. 19 12b: Takano, S.; Sekiguchi, Y.; Sato, N.; Ogasawara, K. Synthesis 1987, 139.
49. 11d: Reinaud, O.; Capdevielle, P.; Maumy, M. Tetrahedron 1987, 43, 4167. 12d: Mukhopadhyay, M.; Reddy, M. M.; Maikap, G. C.; Iqbal, J. J. Org. Chem. 1995, 60, 2670. 12e: Muccioli, A. B.; Simpkins, N. S.; Mortlock, A. J. Org. Chem. 1994, 59, 5141.
50. 11d: Reinaud, O.; Capdevielle, P.; Maumy, M. Tetrahedron 1987, 43, 4167. 12d: Mukhopadhyay, M.; Reddy, M. M.; Maikap, G. C.; Iqbal, J. J. Org. Chem. 1995, 60, 2670. 12e: Muccioli, A. B.; Simpkins, N. S.; Mortlock, A. J. Org. Chem. 1994, 59, 5141.
51. 11d: Reinaud, O.; Capdevielle, P.; Maumy, M. Tetrahedron 1987, 43, 4167. 12d: Mukhopadhyay, M.; Reddy, M. M.; Maikap, G. C.; Iqbal, J. J. Org. Chem. 1995, 60, 2670. 12e: Muccioli, A. B.; Simpkins, N. S.; Mortlock, A. J. Org. Chem. 1994, 59, 5141.