Formation of cyclopropyl carbinols through a highly diastereoselective hydrozirconation of vinyloxirane derivatives

Tetrahedron Letters

Volumn 38, Issue 11, 1997, Pages 1957-1960

  Harada, Susumu ^a   Kowase, Noboru ^a   Taguchi, Takeo ^a   Hanzawa, Yuji ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

METHANOL DERIVATIVE; ZIRCONIUM DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0031575813     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00233-5     Document Type: Article

References (26)

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. 2. Wang, J.-T.; Zhang, Y.-W.; Xu, Y.-M.; Bai, G.-C. Youji Huaxue 1989, 9, 41.
7. 3. (a) Suzuki, K.; Hasegawa, T.; Imai, T.; Maeta, H.; Ohba, S. Tetrahedron 1995, 51, 4483.
8. (b) Copéret, C.; Negishi, E.; Xi, Z.; Takahashi, T. Tetrahedron Lett. 1994, 35, 695.
9. 4. (a) Charette, A. B.; Marcoux, J.-F. Synlett 1995, 1197.
10. (b) Motherwell, W. B.; Nutley, C. J. Contemp. Org. Synth. 1994, 1, 219 and the references cited therein.
11. 5. For example: (a) Johnson, R. A.; Sharpless, K. B. In Comprehensive Organic Synthesis; Paquette. L. A. Ed.; Pergamon Press: Oxford, 1991, Vol. 7, p 389.
12. (b) Finn, M. G.; Sharpless, K. B. In Asymmetric Synthesis; Morrison, J. D. Ed.; Academic Press: Orlando, 1985, Vol. 5, p 247. For the practical preparation of vinyloxirane derivatives, see: Hosomi, A.; Kohra, S.; Tominaga, Y.; Ando, M.; Sakurai, H. Chem. Pham. Bull. 1987, 35, 3058.
13. (b) Finn, M. G.; Sharpless, K. B. In Asymmetric Synthesis; Morrison, J. D. Ed.; Academic Press: Orlando, 1985, Vol. 5, p 247. For the practical preparation of vinyloxirane derivatives, see: Hosomi, A.; Kohra, S.; Tominaga, Y.; Ando, M.; Sakurai, H. Chem. Pham. Bull. 1987, 35, 3058.
14. 6. Although we must await further study on the exact elimination process of the β-alkoxy group, many examples have been reported. Hanzawa, Y.; Ito, H.; Taguchi, T. Synlett 1995, 299 and the references cited therein. See also ref 1a.
15. 7. Annby, U.; Karlsson, S.; Gronowitz, S.; Hallberg, A.; Alvhaell, J.; Svenson, R. Acta Chem. Scand. 1993, 47, 425.
16. 8. For the formation of the cyclopropyl ring by the reactions of alkylzirconocene, see: (a) Takahashi, T.; Xi, Z.; Kotora, M.; Xi, C.; Nakajima, K. Tetrahedron Lett. 1996, 37, 7521.
17. (b) Harris, M. C. J.; Whitby, R. J.; Blagg, J. Tetrahedron Lett. 1995, 36, 4287.
18. (c) Takahashi, T.; Kondakov, D. Y.; Suzuki, N. Tetrahedron Lett. 1993, 39, 6571.
19. (d) Davis, J. M.; Whitby, R. J.; Jaxa-Chamiec, A. Tetrahedron Lett. 1992, 33, 5655.
20. (e) Schwartz, J.; Labinger, J. A. Angew. Chem. Int. Ed. Engl. 1976, 75, 262.
21. 9. To our knowledge, only one example of the diastereoselective hydrozirconation to cyclohexenol derivatives has been reported. Wipf, P.; Xu, W. Synlett 1992, 718.
22. 10. Charette, A. B.; Lebel, H. J. Org. Chem. 1995, 60, 2966. (equation presented)
23. 11. (a) Endo, J.; Koga, N.; Morokuma, K. Organometallics 1993, 12, 2777.
24. (b) Koga, N,; Morokuma, K. Chem. Rev. 1991, 91, 823.
25. 12. The ab initio calculation of the conformers of the model compound 10 suggests that the gauche-form is the most stable conformer. See also: (a) Combs, L. L.; Morgan, A.; Lott, J. Spectoscopy Lett. 1990, 23, 369.
26. (b) Kalasinsky, V. F.; Pechsiri, S. J. Roman Spectroscopy 1980, 9, 120. (equation presented)