Fluorine-containing optically active allylic alcohols: preparation and Claisen rearrangement as a new entry to highly functionalized fluorinated amino alcohol derivatives

Abstract

The reaction of Garner aldehyde 1 with 2-bromo-3,3,3-trifluoropropene in the presence of Zn–Ag couple gave the fluorine-containing, optically active allylic alcohol 2 in 65% yield with a diastereomeric excess greater than 98%. The treatment of Garner aldehyde 1 with CF₃CFBr₂ (3a) and CF₃CCl₃ (3b) in the presence of zinc powder and catalytic AlCl₃ highly diastereoselectively afforded 4a and 4b, respectively, in moderate yield. The orthoester Claisen rearrangement of 4a, b and 2 provided a new way to highly functionalized amino alcohol derivatives 6a–f containing a limited number of fluorine atoms.

References

1. T. Laib, J. Chastanet and J. Zhu, J. Org. Chem., 1998, 63, 1709; K. Hale, D. Menaldino, A. H. Merrill and D. Liotta, Tetrahedron, 1994, 50, 9181; Y. A. Hannun and R. M. Bell, Science, 1989, 243, 500; A. Vidal-Ferran, A. Moyano, M. A. Pericas and A. Riera, J. Org. Chem., 1997, 62, 4970; R. Noyori and M. Kitamura, Angew. Chem., Int. Ed. Engl., 1991, 30, 49; D. J. Ajer, I. Prakash and D. R. Schaad, Chem. Rev., 1996, 96, 835.
2. J. F. Liebman, A. Greenberg and W. R. Dolbier, Fluorine-containing Molecules, Structure, Reactivity, Synthesis and Application, VCH, New York, 1988 ed. R. Filler, Y. Kobayashi and L. M. Yagupolskii, Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications, Elsevier, Amsterdam, 1993.
3. W. Dirk and B. Klaus, Synthesis, 1996, 1421; N. O. Sergey, S. G. Alexander, S. Norbert, M. Thomas, F. K. Alexey, K. F. Alexander and B. Klaus, J. Org. Chem., 1996, 61, 7521.
4. A. R. Sting and D. Seebach, Tetrahedron, 1996, 52, 279; K. Yoshitsugu, N. Takuji, K. Kobee, Y. Yoshinori, K. Kenji and O. Mitsuaki, Tetrahedron: Asymmetry, 1996, 7, 3544; J. T. Welch, Tetrahedron, 1987, 43, 3123.
5. F. J. Sardian and H. Rapoport, Chem. Rev., 1996, 96, 1825; M. T. Reetz, Angew. Chem., Int. Ed. Engl., 1991, 30, 1531.
6. L. Williams, Z. Zhang, F. Shao, P. Carroll and M. M. Joullie, Tetrahedron, 1996, 52, 11673; F. Daniello, A. Schoenfelder, A. Mann and M. Taddei, J. Org. Chem., 1996, 61, 9631.
7. P. Herold, Helv. Chim. Acta, 1988, 71, 354.
8. R. Villard, F. Fotiadu and G. Bouno, Tetrahedron: Asymmetry, 1998, 9, 607.
9. A. Otaka, K. Miyoshi, T. R. Burke, P. P. Roller, H. Kubata, H. Tamamura and N. Fujii, Tetrahedron Lett., 1995, 36, 927.
10. S. Peng, F.-L. Qing and Y.-L. Guo, Synlett, 1998, 859.
11. F. Hong, X. Q. Tang and C. M. Hu, J. Chem. Soc., Chem. Commun., 1994, 289.
12. The crystal data for 2 are as follows: crystal size 0.20 × 0.20 × 0.30 mm; orthorhombic; P2₁2₁2₁ with a=10.10.315(6), b=34.799(8), c=9.715(4)Å, V=3487(2)ų, Z=8, D_calc=1.239 g cm^–3. CCDC reference number 207/362.
13. M. Chérest, H. Felkin and N. Prudent, Tetrahedron Lett., 1968, 18, 2199; N. T. Anh, Top. Curr. Chem., 1980, 88, 145.
14. M. Fujila and I. Hiyama, Tetrahedron Lett., 1986, 27, 3655.
15. X. Q. Tang and C. M. Hu, J. Chem. Soc., Chem. Commun., 1994, 631 (J. Chem. Soc., Perkin Trans. 1, 1994, 2161); J. Fluorine Chem., 1995, 74, 9; H. P. Guan, Q. S. Hu and C. M. Hu, Synthesis, 1996, 997; H. P. Guan, B. H. Luo and C. M. Hu, Synthesis, 1997, 461.
16. The crystal data for 4b are as follows: crystal size 0.20 × 0.20 × 0.30 mm; orthorhombic; P2₁2₁2₁ with a=11.670(3), b=14.278(5), c=10.096(2)Å, V=1682.3(7)ųZ=4, D_calc=1.294 g cm^–3. CCDC reference number 207/362.
17. B. W. Metcalf, E. T. Jarvi and J. P. Burkhart, Tetrahedron Lett., 1985, 26, 2861; H. Greuter, R. W. Lang and A. J. Romann, Tetrahedron Lett., 1988, 29, 3291; S. T. Patel and J. M. Percy, J. Chem. Soc., Chem. Commun., 1992, 1477; S. T. Purrington and S. C. Weeks, J. Fluorine Chem., 1992, 56, 165; S. T. Patel, J. M. Percy and R. D. Wilkes, Tetrahedron, 1995, 51, 11327; T. Takagi, N. Okikawa, S. Johnoshita, M. Koyama, A. Ando and I. Kumadaki, Synlett, 1996, 82; J. M. Percy and R. D. Wilkes, Tetrahedron, 1997, 53, 14749; T. Konno, H. Umetani and T. Kitazume, J. Org. Chem., 1997, 62, 137; T. Yamazaki, H. Umetani and T. Kitazume, Tetrahedron Lett., 1997, 38, 6705; H. Ito, A. Sato, T. Kobayashi and T. Taguchi, Chem. Commun., 1998, 2441; J. M. Percy and M. E. Prime, J. Org Chem., 1998, 63, 8049.
18. W. S. Johnson, L. Werthemann, W. R. Barlett, T. J. Brocksom, T. Li, D. J. Faulkner and M. R. Petersen, J. Am. Chem. Soc., 1970, 92, 741.
19. W. R. Cullen and M. C. Waldman, Can. J. Chem., 1969, 47, 3093.
20. G. W. Daub, J. P. Edwards, C. R. Okada, J. W. Allen, C. T. Maxey, M. S. Wells, A. S. Goldstein, M. J. Dibly, C. J. Wang, D. P. Ostercamp, S. Chung, P. S. Cunningham and M. A. Berliner, J. Org. Chem., 1997, 62, 1976.
21. P. Garner and J. M. Park, Org. Synth., 1991, 70, 18.
22. A. L. Henne and M. Nager, J. Am. Chem. Soc., 1951, 73, 1042.
23. W. J. Miller, E. W. Fager and P. H. Griswald, J. Am. Chem. Soc., 1950, 72, 705.
24. D. J. Burton, PhD Thesis, Cornell University, Ithaca, New York, 1961.