A one-pot synthesis of doubly unsaturated trifluoromethyl amines: Easy access to CF3-substituted piperidines

European Journal of Organic Chemistry

Volumn , Issue 7, 2005, Pages 1258-1265

  Magueur, Guillaume ^a   Legros, Julien ^a   Meyer, Franck ^a   Ourévitch, Michèle ^a   Crousse, Benoit ^a   Bonnet Delpon, Danièle ^a  

^a CNRS   (France)

Author keywords

Allylation; Cyclization; Fluoral; Nitrogen heterocycles; Trifluoromethyl group

Indexed keywords

ACETAL DERIVATIVE; AMINE; FLUORINE DERIVATIVE; FLUOROFORM; HETEROCYCLIC COMPOUND; IMINE; NITROGEN DERIVATIVE; PIPERIDINE DERIVATIVE; TRIFLUOROACETALDIMINE DERIVATIVE; TRIFLUOROMETHYL AMINE DERIVATIVE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CYCLIZATION; PAUSON KHAND REACTION; REACTION ANALYSIS; REPRODUCIBILITY; RING CLOSING METATHESIS; ROOM TEMPERATURE; SYNTHESIS; TECHNIQUE;

EID: 16444381289     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400719     Document Type: Article

References (30)

1. P. S. Watson, B. Jiang, B. Scott, Org. Lett. 2000, 2, 3679-3681, and references cited therein.
2. For a review, see: P. M. Weintraub, J. S. Sabol, J. M. Kane, D. R. Borcherding, Tetrahedron 2003, 39, 2953-2989.
3. a) J.-P Bégué, D. Bonnet-Delpon, Chimie Bioorganique et Médicinale du Fluor, Edisciences-CNRS Publishers, in press;
4. b) Organofluorine Compounds in Medicinal Chemistry and Biochemical Applications (Eds.: R. Filler, Y. Kobayashi, L. Yagupolskii), Elsevier, Amsterdam, 1993;
5. c) Biomedical Frontiers of Fluorine Chemistry (Eds.: I. Ojima, J. R. McCarthy, J. T. Welch), ACS, Washington, 1996;
6. d) P. N. Edwards, in Organofluorine Chemistry: Principles and Commercial Applications (Eds.: R. E. Banks, J. C. Tatlow), Plenum Press. New York, 1994, p. 501.
7. For a review, see: J.-R Bégué, D. Bonnet-Delpon, B. Crousse, J. Legros, manuscript submitted.
8. a) A. Abouabdellah, J.-P. Bégué, D. Bonnet-Delpon, Synlett 1996, 399-400;
9. b) A. Abouabdellah, J.-P. Bégué, D. Bonnet-Delpon, T. T. T. Nga, J. Org. Chem. 1997, 62, 8826-8833.
10. B. Crousse, S. Narizuka, D. Bonnet-Delpon, J.-P. Bégué, Synlett; 2001, 679-681.
11. a) B. Crousse, J.-P. Bégué, D. Bonnet-Delpon, Tetrahedron Lett. 1998, 39, 5765-5768;
12. b) B. Crousse, J.-P. Bégué, D. Bonnet-Delpon, J. Org. Chem. 2000, 65, 5009-5013.
13. For reviews on RCM, see: a) S. K. Armstrong, J. Chem. Soc., Perkin Trans. 1 1998, 371-388;
14. b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043;
15. b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043;
16. c) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29;
17. d) F.-X. Felpin, J. Lebreton, Eur. J. Org. Chem. 2003, 3693-3712;
18. e) A. Deiters, S. F. Martin, Chem. Rev. 2004, 104, 2199-2238.
19. S. Gille, A. Ferry, T. Billard, B. R. Langlois, J. Org. Chem. 2003, 68, 8932-8935.
20. a) J. Legros, F. Meyer, M. Coliboeuf, B. Crousse, D. Bonnet-Delpon, J.-P. Bégué, J. Org. Chem. 2003, 68, 6444-6446.
21. See also: b) D. Bonnet-Delpon, J.-P. Bègué, J. Legros, B. Crousse, F. Meyer (Rhodia Chimie, Fr.) PCT Int. Appl., 2003, WO 2003095415.
22. For a review of the allylation reaction of fluoral and its derivatives, see: D. Bonnet-Delpon, J.-P. Bégué, B. Crousse, in Fluorinated Synthons (Ed.: V. Soloshonok), Oxford University Press, accepted for publication.
23. [10]
24. Diastereoselective allylation of trifluoromethyl aldimines has also been described with allyltin derivatives as allyl donors and SAMP or RAMP as chiral auxiliaries: K. Funabiki, M. Nagamori, M. Matsui, D. Enders, Synthesis 2002, 2585-2588.
25. Homopropargylamine was accompanied by traces of allenyl product.
26. a) I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, M. I. Foreman, J. Chem. Soc., Perkin Trans. 1 1973, 977-981;
27. b) For a review, see: K. M. Brummond, J. L. Kent, Tetrahedron 2000, 56, 3263-3283.
28. The configurations of 25 and 26 were attributed according to homo- and hetero-nOe data.
29. [10a]
30. It is imperative to use zinc as coarse powder. Parallel experiments showed that when using zinc dust in combination with TMSCl, no reaction occurred. As an alternative, zinc dust could be activated by aq. HCl prior to the reaction. However, the results obtained by this latter procedure are not always reproducible.