Enantioselective copper-mediated allylic substitution with Grignard reagents employing a chiral reagent-directing leaving group

Synthesis

Volumn , Issue 1, 2005, Pages 147-157

  Breit, Bernhard ^a,b,c,d,e,f   Breuninger, Daniel ^a,b,f  

^a UNIVERSITY OF FREIBURG   (Germany)

^b Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

^c STANFORD UNIVERSITY   (United States)

^d Harvard University ^*

^e HARVARD UNIVERSITY   (United States)

^f UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Allylic substitution; Asymmetric synthesis; Grignard reagents; Organocopper reagents; Synthetic methods

Indexed keywords

ALLYLIC SUBSTITUTION; ENANTIOSELECTIVITY; GRIGNARD REAGENT; REGIOSELECTIVITY;

COPPER; OPTIMIZATION; PARAMETER ESTIMATION; PHENOLS; PHOSPHORUS COMPOUNDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

SUBSTITUTION REACTIONS;

2 DIPHENYLPHOSPHANYLFERROCENE CARBOXYLATE; ALLYL COMPOUND; COPPER; FERROCENE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ALLYLIC REARRANGEMENT; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; GRIGNARD REACTION; REACTION ANALYSIS;

EID: 12344332728     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-831247     Document Type: Article

References (35)

1. Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395, and references cited therein.
2. (a) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135.
3. (b) Yamamoto, Y. In Houben-Weyl, Methods for Organic Synthesis, Vol. E21b; Thieme: Stuttgart, 1995, 2011-2040.
4. (c) Krause, N.; Gerold, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 186.
5. (d) Breit, B.; Demel, P. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002, 188.
6. Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1984, 25, 3063.
7. (a) Ibuka, T.; Tanaka, M.; Nishii, S.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1987, 1596.
8. (b) Ibuka, T.; Akimoto, N.; Tanaka, M.; Nishii, S.; Yamamoto, Y. J. Org. Chem. 1989, 54, 4055.
9. (c) Harrington-Frost, N.; Leuser, H.; Calaza, M. I.; Kneisel, F. F.; Knochel, P. Org. Lett. 2003, 5, 2111.
10. (a) Barsanti, P.; Calò, V.; Lopez, L.; Marchese, G.; Naso, F.; Pesce, G. J. Chem. Soc., Chem. Commun. 1978, 1085.
11. (b) Calò, V.; Lopez, L.; Carlucci, W. F. J. Chem. Soc., Perkin Trans. 1 1983, 2953.
12. (c) Valverde, S.; Bernabé, M.; Garcia-Ochoa, S.; Gómez, A. M. J. Org. Chem. 1990, 55, 2294.
13. Breit, B.; Demel, P. Adv. Synth. Catal. 2001, 343, 429.
14. Breit, B.; Demel, P.; Studte, C. Angew. Chem. 2004, 116, in press.
15. Denmark, S. E.; Marble, L. K. J. Org. Chem. 1990, 55, 1984.
16. (a) Calò, V.; Nacci, A.; Fiandanese, V. Tetrahedron 1996, 52, 10799.
17. (b) Calò, V.; Fiandanese, V.; Nacci, A.; Scilimati, A. Tetrahedron 1994, 50, 7283.
18. (a) Shu-Li, Y.; Yu-Mei, L.; We-Ping, D.; Xue-Long, H.; Li-Xin, D. J. Organomet. Chem. 2001, 637-639, 845.
19. (b) Stepnicka, P. New J. Chem. 2002, 26, 567.
20. Höfle, G.; Steglich, W.; Vorbrüggen, H. Angew. Chem., Int. Ed. Engl. 1978, 17, 569; Angew. Chem. 1978, 17, 602.
21. Höfle, G.; Steglich, W.; Vorbrüggen, H. Angew. Chem., Int. Ed. Engl. 1978, 17, 569; Angew. Chem. 1978, 17, 602.
22. Bäckvall, J.-E.; Sellén, M.; Grant, B. J. Am. Chem. Soc. 1990, 112, 6615.
23. Schlögl, K. Top. Stereochem. 1967, 1, 39.
24. Persson, E. S. M.; Bäckvall, J.-E. Acta Chem. Scand. 1995, 49. 899.
25. Goeppel, D.; Muenster, I.; Brueckner, R. Tetrahedron 1994, 50, 3687.
26. Eberbach, W.; Trostmann, U. Chem. Ber. 1981, 114, 2979.
27. Couladouros, E. A.; Soufli, I. C.; Moutsos, V. I.; Chadha, R. K. Chem.-Eur. J. 1998, 4, 33.
28. Hayashi, T.; Iwamura, H.; Naito, M.; Matsumoto, Y.; Uozumi, Y.; Miki, M.; Yanaki, K. J. Am. Chem. Soc. 1994, 116, 775.
29. Masuda, Y.; Hoshi, M.; Arase, A. Bull. Chem. Soc. Jpn. 1992, 65, 3294.
30. Metzger, J. O.; Blumenstein, M. Chem. Ber. 1993, 126, 2493.
31. Meuzelaar, G. J.; Karlström, A. S. E.; Klaveren, M. V.; Persson, E. S. M.; Villar, A. D.; Koten, G. V.; Bäckvall, J.-E. Tetrahedron 2000, 56, 2895.
32. Rodríguez, D.; Sestelo, J. P.; Sarandeses, L. A. J. Org. Chem. 2003, 65, 2518.
33. Wenkert, E.; Michelotti, E. L.; Swindell, C. S.; Tingoli, M. J. Org. Chem. 1984, 49, 4894.
34. Denmark, S. E.; Sweis, R. F. Org. Lett. 2002, 4, 3771.
35. Persson, E. S. M.; Klaveren, M. V.; Grove, D. M.; Bäckvall, J. E.; Koten, G. V. Chem.-Eur. J. 1995, 1, 351.