Synthesis of enantiopure α-alkoxy-α-trifluoromethyl aldehydes and carboxylic acids from trifluoromethyl ketones

Angewandte Chemie - International Edition

Volumn 37, Issue 24, 1999, Pages 3428-3430

  Fernández, Rosario ^b   Martín Zamora, Eloísa ^b   Pareja, Carmenj ^b   Vázquez, Juan ^b   Díez, Elena ^b   Monge, Angeles ^c   Lassaletta, José M ^a  

^a INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

^b UNIVERSITY OF SEVILLE   (Spain)

^c INSTITUTO DE CIENCIA DE MATERIALES DE MADRID   (Spain)

Author keywords

Asymmetric synthesis chiral auxiliaries fluorine; Hydrazones; Nucleophilic additions

Indexed keywords

ACETONE; ALDEHYDE; CARBONYL DERIVATIVE; CARBOXYLIC ACID; DIALKYLFORMALDEHYDE HYDRAZONE; FORMALDEHYDE; HYDRAZONE DERIVATIVE; KETONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; METHODOLOGY; PROTEIN QUATERNARY STRUCTURE; SYNTHESIS;

EID: 0033521581     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981231)37:24<3428::AID-ANIE3428>3.0.CO;2-P     Document Type: Article

References (22)

1. a) J. T. Welch, S. Eswarakrishnan, Fluorine in Bioorganic Chemistry, Wiley, New York, 1991;
2. b) Organofluorine Chemistry, Principles and Commercial Applications (Eds.: R. E. Banks, B. E. Smart, J. C. Tatlow), Plenum, New York, 1994.
3. a) T. Ido, K. Fukushi, T. Irie in Biomedicinal Aspects of Fluorine Chemistry (Eds.: R. Filler, Y. Kobayashi), Kodansha, Tokio, and Elsevier, Amsterdam, 1982;
4. b) Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications (Eds.: R. Filler, Y. Kobayashi, L. M. Yagupolskii), Elsevier, Amsterdam, 1993.
5. a) S. Arakawa, K. Nito, J. Seto, J. Mol. Cryst. Liq. 1991, 204, 15;
6. b) R. Buchecker, S. M. Kelly, J. Fünfschilling, Liq. Cryst. 1990, 8, 217;
7. c) T. R. Doyle, O. Vogol, J. Am. Chem. Soc. 1989, 111, 8510;
8. d) Y. Suzuki, T. Hagiwara, I. Kawamura, N. Okamura, T. Kitazume, M. Kakimoto, Y. Imai, Y. Ouchi, H. Takezoe, A. Fukuda, Liq. Cryst. 1989, 6, 167.
9. J. Wiedemann, T. Heiner, G. Mloston, G. K. Surya Prakash, G. Olah, Angew. Chem. 1998, 110, 880-881; Angew. Chem. Int. Ed. 1998, 37, 820-821, and references therein.
10. J. Wiedemann, T. Heiner, G. Mloston, G. K. Surya Prakash, G. Olah, Angew. Chem. 1998, 110, 880-881; Angew. Chem. Int. Ed. 1998, 37, 820-821, and references therein.
11. a) P. Bravo, M. Frigerio, G. Resnati, J. Org. Chem. 1990, 55, 4216-4218;
12. b) A. Dondoni, A. Boscarato, P. Formaglio, J.-P. Bégué, F. Benayoud, Synthesis 1995, 654-658.
13. a) J. M. Lassaletta, R. Fernández, Tetrahedron Lett. 1992, 33, 3691-3694;
14. b) R. Fernández, C. Gasch, J. M. Lassaletta, J. M. Liera, Tetrahedron Lett. 1994, 35, 471 -472;
15. c) D. Enders, R. Syrig, G. Raabe, R. Fernández, C. Gasch, J. M. Lassaletta, J. M. Liera, Synthesis 1996, 48-52;
16. d) J. M. Lassaletta, R. Fernández, C. Gasch, J. Vazquez, Tetrahedron 1996, 52, 9143-9160.
17. J. M. Lassaletta, R. Fernández, E. Martín-Zamora, E. Díez, J. Am. Chem. Soc. 1996, 118, 7002-7003;
18. b) E. Díez, F. Fernández, C. Gasch, J. M. Lassaletta, J. M. Llera, E. Martín-Zamora, J. Vázquez, J. Org. Chem. 1997, 62, 5144-5155.
19. J. M. Lassaletta, R. Fernández, E. Martín-Zamora, C. Pareja, Tetrahedron Lett. 1996, 37, 5787-5790.
20. 2; conventional R factors are based on F. The configuration of C(5) is based on that known for the auxiliary. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC-102999. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
21. D. J. Bailey, D. O'Hagan, M. Tavasli, Tetrahedron: Asymmetry 1997, 8, 149-153.
22. D. Enders, H. Kipphardt, P. Gerdes, L. J. Breña-Valle, V. Buhshan, Bull. Soc. Chim. Belg. 1988, 97, 691-704.