Improving enantioselective fluorination reactions: Chiral N-fluoroammonium salts and transition metal catalysts

Angewandte Chemie - International Edition

Volumn 40, Issue 9, 2001, Pages 1653-1656

  Muñiz, Kilian ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

Asymmetric catalysis; Asymmetric synthesis; Fluoroorganic compounds; Homogeneous catalysis; Transition metals

Indexed keywords

CATALYSTS; DERIVATIVES; ELECTROPHORESIS; SUBSTRATES;

CHIRAL CATALYSTS;

FLUORINE COMPOUNDS;

AMMONIUM DERIVATIVE; FLUORIDE; METAL;

CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; FLUORINATION; SHORT SURVEY;

EID: 0038584547     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20010504)40:9<1653::AID-ANIE16530>3.0.CO;2-W     Document Type: Short Survey

References (41)

1. a) Enantiocontrolled Synthesis of Fluoro-Organic Compounds (Ed.: V. A. Soloshonok), Wiley, New York, 1999;
2. b) "Asymmetric Fluoroorganic Chemistry, Applications, and Future Directions": P. V. Ramachandran, ACS Symp. Ser. 2000, 746.
3. G. L. Hann, P. Sampson, J. Chem. Soc. Chem. Commun. 1989, 1650-1651.
4. S. D. Taylor, C. C. Kotoris, G. Hum. Tetrahedron 1999, 55, 12431-12477.
5. G. S. Lal, G. P. Pez, R. G. Syvret, Chem. Rev. 1996, 96, 1737-1755.
6. a) F. A. Davies, P. V. N. Kasu, Org. Prep. Proced. Int. 1999, 31, 125-143;
7. see also: b) F. A. Davies, P. V. N. Kasu, Tetrahedron Lett. 1998, 39, 6135-6138;
8. c) F. A. Davies, W. Han, Tetrahedron Lett. 1992, 33, 1153-1156;
9. d) F. A. Davies, R. E. Reddy, Tetrahedron: Asymmetry 1994, 5, 955-960;
10. e) D. Enders, M. Potthoff, G. Raabe, J. Runsink, Angew. Chem. 1997, 109, 2454-2456; Angew. Chem. Int. Ed. Engl. 1997, 36, 2362-2364;
11. e) D. Enders, M. Potthoff, G. Raabe, J. Runsink, Angew. Chem. 1997, 109, 2454-2456; Angew. Chem. Int. Ed. Engl. 1997, 36, 2362-2364;
12. f) J. J. McAtee, R. F. Schinazi, D. C. Liotta, J. Org. Chem. 1998, 63, 2161-2167.
13. E. Differding, R. W. Lang, Tetrahedron Lett. 1988, 29, 6087-6090.
14. a) F. A. Davies, P. Zhou, C. K. Murphy, Tetrahedron Lett. 1993, 34, 3971-3974;
15. b) F. A. Davies, P. Zhou, C. K. Murphy, G. Sundarababu, H. Qi, W. Han, R. M. Przeslawski, B.-C. Chen, P. J. Caroll, J. Org. Chem. 1998, 63, 2273-2280;
16. c) F. A. Davies, P. Zhou, C. K. Murphy, G. Sundarababu, H. Qi, W. Han, R. M. Przeslawski, B.-C. Chen, P. J. Caroll, J. Org. Chem. 1998, 63, 9604.
17. Y. Takeuchi, T. Suzuki, A. Satoh, T. Shiragami, N. Shibata, J. Org. Chem. 1999, 64, 5708-5711.
18. a) Y. Takeuchi, A. Satoh, T. Suzuki, A. Kameda, M. Dohrin, T. Satoh, T. Koizumi, K. L. Kirk, Chem. Pharm. Bull. 1997, 45, 1085-1088;
19. b) see also: Z. Liu, N. Shibata, Y. Takeuchi, J. Org. Chem. 2000, 65, 7583-7587, and literature therein.
20. N. Shibata, E. Suzuki, Y. Takeuchi, J. Am. Chem. Soc. 2000, 122, 10728-10729.
21. R. E. Banks, J. Fluorine Chem. 1998, 87, 1-17.
22. D. Cahard, C. Audouard, J.-C. Plaquevent, N. Roques, Org. Lett. 2000, 2, 3699-3701.
23. For a first isolation of the chiral ammonium salt of quinuclidine, see: M. Abdul-Ghani, R. E. Banks, M. K. Besheesh, I. Sharif, R. G. Syvret, J. Fluorine Chem. 1995, 73, 255-257.
24. Lectka and co-workers have recently described an impressive asymmetric α-chlorination reaction (up to 99% ee) in which the stereoselective step relies on only a catalytic amount of cinchona alkaloid: H. Wack, A. E. Taggi, A. M. Hafez, W. J. Drury III, T. Lectka, J. Am. Chem. Soc. 2001, 123, 1531-1532.
25. a) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994;
26. b) Transition Metals for Organic Synthesis (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 1998;
27. c) Catalytic Asymmetric Synthesis (Ed.: I. Ojima), 2nd ed., Wiley-VCH, New York, 2000;
28. d) Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999.
29. S. Bruns, G. Haufe, J. Fluorine Chem. 2000, 104, 247-254.
30. a) E. N. Jacobsen, Acc. Chem. Res. 2000, 33, 421-431;
31. b) R. G. Konsler, J. Karl, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 129, 10780-10781;
32. c) apparently, ARO with other halide sources also does not proceed with high enantiosdectivity (ref. [17a]).
33. a) Formation of competing nucleophiles might be prevented by use of fluorinated chiral Lewis acid catalysts:
34. b) B. L. Pagenkopf, E. N. Carreira, Chem. Eur. J. 1999, 5, 3437-3442.
35. L. Hintermann, A. Togni, Angew. Chem. 2000, 112, 4530-4533; Angew. Chem. Int. Ed. 2000, 39, 4359-4362.
36. L. Hintermann, A. Togni, Angew. Chem. 2000, 112, 4530-4533; Angew. Chem. Int. Ed. 2000, 39, 4359-4362.
37. TADDOL = 2.2-dimethyl-α,α,α′,α′-tetraaryl-1,3- dioxolane-4,5-dimethanol.
38. a) S. Shambayati, S. L. Schreiber, J. A. Ragau, R. F. Standaert in Strategies and Tactics in Organic Synthesis, Vol. 3 (Ed.: T. Lindberg), Academic Press, San Diego. 1991, pp. 417-461;
39. b) Lewis Acids in Organic Synthesis (Ed.: H. Yamamoto), Wiley-VCH, Weinheim, 2000.
40. The related reactions regarding chlorination and bromination have also been described: L. Hintermann, A. Togni, Helv. Chim. Acta 2000, 83, 2425-2435.
41. For a complementary approach of enantioselective enolization by aid of chiral amide base and subsequent fluorination with achiral 4, see: A. Armstrong, B. R. Hayter, Chem. Commun. 1998, 621-622.