Diastereoselective synthesis of β-amino-α-(trifluoromethyl) alcohols from homochiral α-dibenzylamino aldehydes

European Journal of Organic Chemistry

Volumn , Issue 7, 2004, Pages 1558-1566

  Andrés, José M ^a   Pedrosa, Rafael ^a   Pérez Encabo, Alfonso ^a  

^a UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

Alcohols; Amino aldehydes; Asymmetric Synthesis; Fluorine; Trifluoromethylation

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; AMINO ACID DERIVATIVE; SILANE DERIVATIVE; TRIMETHYL(TRIFLUOROMETHYL)SILANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHIRALITY; METHYLATION; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; SWERN OXIDATION; TEMPERATURE DEPENDENCE;

EID: 4544235069     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300659     Document Type: Article

References (31)

1. For recent reviews see: [1a] R. P. Singh, J. M. Shreeve, Tetrahedron 2000, 56, 7613-7632.
2. [1b] G. K. S. Prakash, A. K. Yudin, Chem. Rev. 1997, 97, 757-786.
3. [1c] R. E. Banks, B. E. Smart, J. C. Tatlow (Eds.), Organofluorine Chemistry: Principles and Commercial Applications, Plenum, New York, 1994.
4. [2a] T. Katagiri, Y. Fujiwara, S. Takahashi, N. Ozaki, K. Uneyama, Chem. Commun. 2002, 986-987.
5. [2b] Y. Fijiwara, T. Katagiri, K. Uneyama, Tetrahedron Lett. 2003, 44, 6161-6163.
6. [3a] D. V. Patel, K. Rielly-Gauvin, D. E. Ryono, C. A. Free, S. A. Smith, E. W. Pertillo Jr., J. Med. Chem. 1993, 36, 2431-2447.
7. [3b] P. R. Bernstein, B. C. Gomes, B. J. Kosmider, E. P. Vacek, J. C. Williams, J. Med. Chem. 1995, 38, 212-215.
8. J. W. Skiles, V. Fuchs, C. Miao, R. Sorcek, K. G. Grozinger, S. C. Mauldin, J. Vitous, P. W. Mui, S. Jacober, G. Chow, M. Matteo, M. Skoog, S. M. Weldon, G. Possanza, J. Keirns, G. Letts, S. S. Rosenthal, J. Med. Chem. 1992, 35, 641-662.
9. [5a] M. W. Walter, A. Felici, M. Galleni, R. P. Soto, R. M. Adlington, J. E. Baldwin, J.-M. Frère, M. Gololobov, C. J. Schofield, Bioorg. Med. Chem. Lett. 1996, 6, 2455-2458.
10. [5b] M. W. Walter, R. M. Adlington, J. E. Baldwin, C. J. Schofield, Tetrahedron 1997, 53, 7275-7290.
11. E-L. Qing, S. Peng, C.-M. Hu, J. Fluorine Chem. 1998, 88, 79-81.
12. P. D. Edwards, Tetrahedron Lett. 1992, 33, 4279-4282.
13. T. Tomayasu, K. Tomooka, T. Nakai, Synlett 1998, 1147-1149.
14. J.-P. Begué, D. Bonnet-Delpon, H. Sdassi, Tetrahedron Lett. 1992, 33, 1879-1882.
15. P. V. Ramachandran, B. Gong, H. C. Brown, J. Org. Chem. 1995, 60, 41-46.
16. J.-P. Begué, D. Bonnet-Delpon, N. Fischer-Durand, A. Amour, M. Reboud-Ravaux, Tetrahedron: Asymmetry 1994, 5, 1099-1110.
17. A. Abouabdellah, J.-P. Begué, D. Bonnet-Delpon, A. Kornilov, I. Rodrigues, C. Richard, J. Org. Chem. 1998, 63, 6529-6534.
18. B. Imperiali, R. H. Abeles, Tetrahedron Lett. 1986, 27, 135-138.
19. D. V. Patel, K. Rielly-Gauvin, D. E. Ryono, Tetrahedron Lett. 1988, 29, 4665-4668.
20. G. K. S. Prakash, M. Mandal, S. Schweizer, N. A. Petasis, G. A. Olah, Org. Lett. 2000, 2, 3173-3176.
21. [16a] J. M. Andrés, R. Barrio, M. A. Martinez, R. Pedrosa, A. Pérez-Encabo, J. Org. Chem. 1996, 61, 4210-4213.
22. [16b] J. M. Andrés, R. Pedrosa, Tetrahedron 1998, 54, 5607-5616.
23. [16c] J. M. Andrés, R. Pedrosa, A. Pérez, A. Pérez-Encabo, Tetrahedron 2001, 57, 8521-8530.
24. [17a] A. A. H. van der Zeijden, Tetrahedron: Asymmetry 1995, 6, 913-918.
25. [17b] K. Ishimaru, K. Tsuru, K. Yabuta, M. Wada, Y. Yamamoto, K. Akiba, Tetrahedron 1996, 52, 13137-13144.
26. [18a] A. Hafner, R. O. Duthaler, R. Marti, G. Rihs, P. Rothe-Streit, F. Schwarzenbach, J. Am. Chem. Soc. 1992, 114, 2321-2336.
27. [18b] R. Villard, F. Fotiadu, G. Buono, Tetrahedron: Asymmetry 1998, 9, 607-611.
28. [19a] M. N. Dufour, P. Jouin, J. Poncet, A. Pantaloni, B. Castro, J. Chem. Soc., Perkin Trans. 1 1986, 1895-1899.
29. [19b] T. Yamazaki, H. Iwatsubo, T. Kitazume, Tetrahedron: Asymmetry 1994, 5, 1823-1830.
30. H. Tokuyama, S. Yokoshima, S.-C. Lin, L. Li, T. Fukuyama, Synthesis 2002, 1121-1123.
31. CCDC-230609 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/ retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: (internat.) + 44-1223-336-033; E-mail: deposit@ccdc.cam.ac.uk].